The compound was purified by silica gel column chromatography (hexanes to 10% ethyl acetate in hexanes). C was treated with potassium bis(trimethylsilyl)amide (KHMDS, 0.5 M, 1.5 mL, 0.75 mmol) and stirred for 1 h at ?78 C. N-phenylbis-(triflouromethanesulfonamide) (323 mg, 0.905 mmol), was added, and the reaction was stirred at ?78 C for 2 h, then slowly warmed to room temperature and quenched with saturated NH4Cl. The compound was extracted with ethyl acetate. The organic phase was washed Soblidotin with water, dried over Na2SO4 and concentrated under reduced pressure. The compound was purified by silica gel column chromatography (hexanes to 10% ethyl acetate in hexanes). Yield: 58%. 13H NMR (400 MHz, CDCl3) : 5.5 (s, 1H), 4.9 (s, 1H), 1.9 (s, 3H), 0.9 (s, 3H), 0.7 (s, 3H). 2.2.2. 3-Acetoxy-17-(3-pyridyl)-5-androsta-16-ene (4) A suspension of compound 3 (550 mg, 1.18 mmol), diethyl-3-pyridylborane (265 mg, 1.81 mmol), bis(triphenylphosphine)palladium (II) chloride (8.12 mg, 0.0116 mmol) in THF (8 mL) was added to an aqueous solution of sodium carbonate (2 M, 5 mL). The mixture was refluxed for 4 h under N2. The reaction was concentrated under reduced pressure, and the residue was extracted with diethylether; the organic phase was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The compound was purified on florisil column chromatography (hexanes to 50% ethyl acetate in hexanes). Yield: 42%. 13C NMR (400 MHz, CDCl3) : 170.6, 151.7, 147.8, 143.7, 140.8, 133.6, 129.1, 122.9, 69.9, 21.5, 11.3, 9.1. 2.2.3. 17-(3-pyridyl)-5-androsta-16-ene-3-ol (5) Compound 4 (470 mg, 1.2 mmol) was dissolved in methanol (5 mL) at room temperature. A solution of KOH (10%) in methanol (3.5 mL) was added, and the mixture was stirred for 1.5 h, then concentrated under reduced pressure. Dichloromethane (25 mL) and water (25 mL) were added, and the mixture was stirred for 1 h. The organic phase was dried over Na2SO4. The compound was purified on florisil column chromatography (hexanes to 50% ethyl acetate in hexanes). Yield: 68%, purity 99.3% by HPLC. 1H NMR (400 MHz, CDCl3) : 8.6 (s, 1H), 8.4 (d, J = 4.8, 1H), 7.6 (d, J = 7.6, 1H), 7.2 (dd, J1 = 4.8 Hz and J2 = 7.6 Hz, 1H), 5.9 (d, J = 1.6 Hz), 4.0 (m, 1H), 2.2 (d, 1H), 2.0 (t, 2H), 1.2-1.8 (m, 17H), 0.9 (s, 3H), 0.8 (s, 3H). 13C NMR (400 MHz, CDCl3) : 151.5, 147.4, 147.3, 133.9, 133.1, 129.3, 123.1, 66.3, 57.5, 54.5, 47.5, 39.3, 36.2, 35.3, 34.0, 31.8, 31.7, 29.0, 28.4, 20.7, 16.7, 11.2. Measured m/z for [M+H] = 352.2642 and predicted m/z = 352.2635. 2.2.4. 17-(3-pyridyl)- 5-androsta-16-ene-3-one (6) To a solution of compound 5 (50 mg, 0.14 mmol) in acetone (4 mL), chromic acid 10% (w/v) (4.5 mL) was drop-wise added at 0 C. The mixture was stirred at room temperature for 3 h, and a solution of sodium bicarbonate was then added to a pH = 7. The reaction mixture was extracted with ethyl acetate, and the organic phase was washed with water and dried over Na2SO4. The compound was purified on silica gel column chromatography (hexanes to 40% ethyl acetate in hexanes). Yield: 30%, purity 99.4%. 1H NMR (400 MHz, CDCl3) : 8.6 (s, 1H), 8.4 (d, J = 4.8, 1H), 7.6 (d, J = 7.6, 1H), 7.2 (dd, J1 = 4.8 Hz and J2 = 7.6 Hz, 1H), 5.9 (d, J = 1.6 Hz), 2.4-1.2 (m, 20H), 1.1 (s, 3H), 1.0 (s, 3H). 13C NMR (400 MHz, CDCl3) : 211.8, 151.5, 147.4, 147.3, 134.2, 133.1, 129.3, 123.1, 66.3, 57.5, 54.5, 47.5, 39.3, 36.2, 35.3, 34.0, 31.8, 31.7, 29.0, 28.4, 20.7, 16.7, Soblidotin 11.2. Measured m/z for [M+H] = 350.2489 and predicted m/z = 350.2478. 2.2.5. 17-Iodoandrosta-5,16-dien-3-ol (9) Into a 100 mL round-bottomed flask, fitted with a magnetic stirring bar, was placed dehydroepiandrosterone (7) (1 g, 3.47 mmol) and ethanol (18 mL). Hydrazine hydrate solution (4.5 mL, 67.3 mmol) was added followed by a solution of hydrazine sulfate (0.05 g, 0.384 mmol) in water (0.5 mL). After stirring at room temperature during 18 h, the mixture was poured into cold water. The precipitate was collected by filtration and dried at room temperature to yield the hydrazone 8 (96% yield). To a solution of compound 8 (2.3 g, 7.61 mmol) and triethylamine (9 mL, 64.82 mmol) in dioxane.1H NMR (400 MHz, CDCl3) : 6.1 (d, 1H), 5.3 (d, 1H), 3.5 (m, 1H), 1.(s, 3H), 0.7 (s, 3H). 2.2.6. stirred at ?78 C for 2 h, then slowly warmed to room temperature and quenched with saturated NH4Cl. The compound was extracted with ethyl acetate. The organic phase was washed with water, dried over Na2SO4 and concentrated under reduced pressure. The compound was purified by silica gel column chromatography (hexanes to 10% ethyl acetate in hexanes). Yield: 58%. 13H NMR (400 MHz, CDCl3) : 5.5 (s, 1H), 4.9 (s, 1H), 1.9 (s, 3H), 0.9 (s, 3H), 0.7 (s, 3H). 2.2.2. 3-Acetoxy-17-(3-pyridyl)-5-androsta-16-ene (4) A suspension of compound 3 (550 mg, 1.18 mmol), diethyl-3-pyridylborane (265 mg, 1.81 mmol), bis(triphenylphosphine)palladium (II) chloride (8.12 mg, 0.0116 mmol) in THF (8 mL) was added to an aqueous solution of sodium carbonate (2 M, 5 mL). The mixture was refluxed for 4 h under N2. The reaction was concentrated under reduced pressure, and the residue was extracted with diethylether; the organic phase was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The compound was purified on florisil column chromatography (hexanes to 50% ethyl acetate in hexanes). Yield: 42%. 13C NMR (400 MHz, CDCl3) : 170.6, 151.7, 147.8, 143.7, 140.8, 133.6, 129.1, 122.9, 69.9, 21.5, 11.3, 9.1. 2.2.3. 17-(3-pyridyl)-5-androsta-16-ene-3-ol (5) Compound 4 (470 mg, 1.2 mmol) was dissolved in methanol (5 mL) at room temperature. A solution of KOH (10%) in methanol (3.5 mL) was added, and the mixture was stirred for 1.5 h, then concentrated under reduced pressure. Dichloromethane (25 mL) and water (25 mL) were added, and the mixture was stirred for 1 h. The organic phase was dried over Na2SO4. The compound was purified on florisil column chromatography (hexanes to 50% ethyl acetate in hexanes). Yield: 68%, purity 99.3% by HPLC. 1H NMR (400 MHz, CDCl3) : 8.6 (s, 1H), 8.4 (d, J = 4.8, 1H), 7.6 (d, J = 7.6, 1H), 7.2 (dd, J1 = 4.8 Hz and J2 = 7.6 Hz, 1H), 5.9 (d, J = 1.6 Hz), 4.0 (m, 1H), 2.2 (d, 1H), 2.0 (t, 2H), 1.2-1.8 (m, 17H), 0.9 (s, 3H), 0.8 (s, 3H). 13C NMR (400 MHz, CDCl3) : 151.5, 147.4, 147.3, 133.9, 133.1, 129.3, 123.1, 66.3, 57.5, 54.5, 47.5, 39.3, 36.2, 35.3, 34.0, 31.8, 31.7, 29.0, 28.4, 20.7, 16.7, 11.2. Measured m/z for [M+H] = 352.2642 and predicted m/z = 352.2635. 2.2.4. 17-(3-pyridyl)- 5-androsta-16-ene-3-one (6) To a solution of compound 5 (50 mg, 0.14 mmol) in acetone (4 mL), chromic acid 10% (w/v) (4.5 mL) was drop-wise added at 0 C. The mixture was stirred at area heat range for 3 h, and a remedy of sodium bicarbonate was after that put into a pH = 7. The response mix was extracted with ethyl acetate, as well as the organic stage was cleaned with drinking water and dried out over Na2Thus4. The chemical substance was purified on silica gel column chromatography (hexanes to 40% ethyl acetate in hexanes). Produce: 30%, purity 99.4%. 1H NMR (400 MHz, CDCl3) : 8.6 (s, 1H), 8.4 (d, J = 4.8, 1H), 7.6 (d, J = 7.6, 1H), 7.2 (dd, J1 = 4.8 Hz and J2 = 7.6 Hz, 1H), 5.9 (d, J = 1.6 Hz), 2.4-1.2 (m, 20H), 1.1 (s, 3H), 1.0 (s, 3H). 13C NMR (400 MHz, CDCl3) : 211.8, 151.5, 147.4, 147.3, 134.2, 133.1, 129.3, 123.1, 66.3, 57.5, 54.5, 47.5, 39.3, 36.2, 35.3, 34.0, 31.8, 31.7, 29.0, 28.4, 20.7, 16.7, 11.2. Assessed m/z for [M+H] = 350.2489 and forecasted m/z = 350.2478. 2.2.5. 17-Iodoandrosta-5,16-dien-3-ol (9) Right into a 100 mL round-bottomed flask, installed using a magnetic stirring club, was positioned dehydroepiandrosterone (7) (1 g, 3.47 mmol) and ethanol.Produce: 68%, purity 99.3% by HPLC. 2.2.1. 3-Acetoxy-5-androsta-16-ene-17-yl-trifluoromethanesulfonate (3) A remedy of substance 2 (250 mg, 0.752 mmol) in tetrahydrofuran (3 mL) in -78 C was treated with potassium bis(trimethylsilyl)amide (KHMDS, 0.5 M, 1.5 mL, 0.75 mmol) and stirred for 1 h at ?78 C. N-phenylbis-(triflouromethanesulfonamide) (323 mg, 0.905 mmol), was added, as well as the response was stirred at ?78 C for 2 h, then slowly warmed to area temperature and quenched with saturated NH4Cl. The chemical substance was extracted with ethyl acetate. The organic stage was cleaned with water, dried out over Na2Thus4 and focused under decreased pressure. The chemical substance was purified by silica gel column chromatography (hexanes to 10% ethyl acetate in hexanes). Produce: 58%. 13H NMR (400 MHz, CDCl3) : 5.5 (s, 1H), 4.9 (s, 1H), 1.9 (s, 3H), 0.9 (s, 3H), 0.7 (s, 3H). 2.2.2. 3-Acetoxy-17-(3-pyridyl)-5-androsta-16-ene (4) A suspension system of substance 3 (550 mg, 1.18 mmol), diethyl-3-pyridylborane (265 mg, 1.81 mmol), bis(triphenylphosphine)palladium (II) chloride (8.12 mg, 0.0116 mmol) in THF (8 mL) was put into an aqueous solution of sodium carbonate (2 M, 5 mL). The mix was refluxed for 4 h under N2. The response was focused under decreased pressure, as well as the residue was extracted with diethylether; the organic stage was cleaned with brine, dried out over Na2Thus4 and focused under decreased pressure. The chemical substance was purified on florisil column chromatography (hexanes to 50% ethyl acetate in hexanes). Produce: 42%. 13C NMR (400 Soblidotin MHz, CDCl3) : 170.6, 151.7, 147.8, 143.7, 140.8, 133.6, 129.1, 122.9, 69.9, 21.5, 11.3, 9.1. 2.2.3. 17-(3-pyridyl)-5-androsta-16-ene-3-ol (5) Substance 4 (470 mg, 1.2 mmol) was dissolved in methanol (5 mL) at area temperature. A remedy of KOH (10%) in methanol (3.5 mL) was added, as well as the mix was stirred for 1.5 h, then focused under decreased pressure. Dichloromethane (25 mL) and drinking water (25 mL) had been added, as well as the mix was stirred for 1 h. The organic stage was dried out over Na2Thus4. The chemical substance was purified on florisil column chromatography (hexanes to 50% ethyl acetate in hexanes). Produce: 68%, purity 99.3% by HPLC. 1H NMR (400 MHz, CDCl3) : 8.6 (s, 1H), 8.4 (d, J = 4.8, 1H), 7.6 (d, J = 7.6, 1H), 7.2 (dd, J1 = 4.8 Hz and J2 = 7.6 Hz, 1H), 5.9 (d, J = 1.6 Hz), 4.0 (m, 1H), 2.2 (d, 1H), 2.0 (t, 2H), 1.2-1.8 (m, 17H), 0.9 (s, 3H), 0.8 (s, 3H). 13C NMR (400 MHz, CDCl3) : 151.5, 147.4, 147.3, 133.9, 133.1, 129.3, 123.1, 66.3, 57.5, 54.5, 47.5, 39.3, 36.2, 35.3, 34.0, 31.8, 31.7, 29.0, 28.4, 20.7, 16.7, 11.2. Assessed m/z for [M+H] = 352.2642 and predicted m/z = 352.2635. 2.2.4. 17-(3-pyridyl)- 5-androsta-16-ene-3-one (6) To a remedy of substance 5 (50 mg, 0.14 mmol) in acetone (4 mL), chromic acidity 10% (w/v) (4.5 mL) was drop-wise added at 0 C. The mix was stirred at area heat range for 3 h, and a remedy of sodium bicarbonate was after that put into a pH = 7. The response mix was extracted with ethyl acetate, as well as the organic stage was cleaned with drinking water and dried out over Na2Thus4. The chemical substance was purified on silica gel column chromatography (hexanes to 40% ethyl acetate in hexanes). Produce: 30%, purity 99.4%. 1H NMR (400 MHz, CDCl3) : 8.6 (s, 1H), 8.4 (d, J = 4.8, 1H), 7.6 (d, J = 7.6, 1H), 7.2 (dd, J1 = 4.8 Hz and J2 = 7.6 Hz, 1H), 5.9 (d, J = 1.6 Hz), 2.4-1.2 (m, 20H), 1.1 (s, 3H), 1.0 (s, 3H). 13C NMR (400 MHz, CDCl3) : 211.8, 151.5, 147.4, 147.3, 134.2, 133.1, 129.3, 123.1, 66.3, 57.5, 54.5, 47.5, 39.3, 36.2, 35.3, 34.0, 31.8, 31.7, 29.0, 28.4, 20.7, 16.7, 11.2. Assessed m/z for [M+H] = 350.2489 and forecasted m/z = 350.2478. 2.2.5. 17-Iodoandrosta-5,16-dien-3-ol (9).Produce: 68%, purity 99.3% by HPLC. slowly warmed to area temperature and quenched with saturated NH4Cl. The chemical substance was extracted with ethyl acetate. The organic stage was cleaned with water, dried out over Na2Thus4 and focused under decreased pressure. The chemical substance was purified by silica gel column chromatography (hexanes to 10% ethyl acetate in hexanes). Produce: 58%. 13H NMR (400 MHz, CDCl3) : 5.5 (s, 1H), 4.9 (s, 1H), 1.9 (s, 3H), 0.9 (s, 3H), 0.7 (s, 3H). 2.2.2. 3-Acetoxy-17-(3-pyridyl)-5-androsta-16-ene Rabbit polyclonal to Receptor Estrogen alpha.ER-alpha is a nuclear hormone receptor and transcription factor.Regulates gene expression and affects cellular proliferation and differentiation in target tissues.Two splice-variant isoforms have been described. (4) A suspension system of substance 3 (550 mg, 1.18 mmol), diethyl-3-pyridylborane (265 mg, 1.81 mmol), bis(triphenylphosphine)palladium (II) chloride (8.12 mg, 0.0116 mmol) in THF (8 mL) was put into an aqueous solution of sodium carbonate (2 M, 5 mL). The mix was refluxed for 4 h under N2. The response was focused under decreased pressure, as well as the residue was extracted with diethylether; the organic stage was cleaned with brine, dried out over Na2Thus4 and focused under decreased pressure. The chemical substance was purified on florisil column chromatography (hexanes to 50% ethyl acetate in hexanes). Produce: 42%. 13C NMR (400 MHz, CDCl3) : 170.6, 151.7, 147.8, 143.7, 140.8, 133.6, 129.1, 122.9, 69.9, 21.5, 11.3, 9.1. 2.2.3. 17-(3-pyridyl)-5-androsta-16-ene-3-ol (5) Substance 4 (470 mg, 1.2 mmol) was dissolved in methanol (5 mL) at area temperature. A remedy of KOH (10%) in methanol (3.5 mL) was added, as well as the mix was stirred for 1.5 h, then focused under decreased pressure. Dichloromethane (25 mL) and drinking water (25 mL) had been added, as well as the mix was stirred for 1 h. The organic stage was dried out over Na2Thus4. The chemical substance was purified on florisil column chromatography (hexanes to 50% ethyl acetate in hexanes). Produce: 68%, purity 99.3% by HPLC. 1H NMR (400 MHz, CDCl3) : 8.6 (s, 1H), 8.4 (d, J = 4.8, 1H), 7.6 (d, J = 7.6, 1H), 7.2 (dd, J1 = 4.8 Hz and J2 = 7.6 Hz, 1H), 5.9 (d, J = 1.6 Hz), 4.0 (m, 1H), 2.2 (d, 1H), 2.0 (t, 2H), 1.2-1.8 (m, 17H), 0.9 (s, 3H), 0.8 (s, 3H). 13C NMR (400 MHz, CDCl3) : 151.5, 147.4, 147.3, 133.9, 133.1, 129.3, 123.1, 66.3, 57.5, 54.5, 47.5, 39.3, 36.2, 35.3, 34.0, 31.8, 31.7, 29.0, 28.4, 20.7, 16.7, 11.2. Assessed m/z for [M+H] = 352.2642 and predicted m/z = 352.2635. 2.2.4. 17-(3-pyridyl)- 5-androsta-16-ene-3-one (6) To a remedy of substance 5 (50 mg, 0.14 mmol) in acetone (4 mL), chromic acidity 10% (w/v) (4.5 mL) was drop-wise added at 0 C. The mix was stirred at area heat range for 3 h, and a remedy of sodium bicarbonate was after that put into a pH = 7. The response mix was extracted with ethyl acetate, as well as the organic stage was cleaned with drinking water and dried out over Na2Thus4. The chemical substance was purified on silica gel column chromatography (hexanes to 40% ethyl acetate in hexanes). Produce: 30%, purity 99.4%. 1H NMR (400 MHz, CDCl3) : 8.6 (s, 1H), 8.4 (d, J = 4.8, 1H), 7.6 (d, J = 7.6, 1H), 7.2 (dd, J1 = 4.8 Hz and J2 = 7.6 Hz, 1H), 5.9 (d, J = 1.6 Hz), 2.4-1.2 (m, 20H), 1.1 (s, 3H), 1.0 (s, 3H). 13C NMR (400 MHz, CDCl3) : 211.8, 151.5, 147.4, 147.3, 134.2, 133.1, 129.3, 123.1, 66.3, 57.5, 54.5, 47.5, 39.3, 36.2, 35.3, 34.0, 31.8, 31.7, 29.0, 28.4, 20.7, 16.7, 11.2. Assessed m/z for [M+H] = 350.2489 and forecasted m/z = 350.2478. 2.2.5. 17-Iodoandrosta-5,16-dien-3-ol (9) Right into a 100 mL round-bottomed flask, installed using a magnetic stirring club, was positioned dehydroepiandrosterone (7) (1 g, 3.47 mmol) and ethanol (18 mL). Hydrazine hydrate alternative (4.5 mL, 67.3 mmol) was added accompanied by a.Assessed m/z for [M+H]= 350.2481 and predicted m/z = 350.2478. 2.3. at ?78 C. N-phenylbis-(triflouromethanesulfonamide) (323 mg, 0.905 mmol), was added, as well as the response was stirred at ?78 C for 2 h, then slowly warmed to area temperature and quenched with saturated NH4Cl. The chemical substance was extracted with ethyl acetate. The organic stage was cleaned with water, dried out over Na2Thus4 and focused under decreased pressure. The chemical substance was purified by silica gel column chromatography (hexanes to 10% ethyl acetate in hexanes). Produce: 58%. 13H NMR (400 MHz, CDCl3) : 5.5 (s, 1H), 4.9 (s, 1H), 1.9 (s, 3H), 0.9 (s, 3H), 0.7 (s, 3H). 2.2.2. 3-Acetoxy-17-(3-pyridyl)-5-androsta-16-ene (4) A suspension system of substance 3 (550 mg, 1.18 mmol), diethyl-3-pyridylborane (265 mg, 1.81 mmol), bis(triphenylphosphine)palladium (II) chloride (8.12 mg, 0.0116 mmol) in THF (8 mL) was put into an aqueous solution of sodium carbonate (2 M, 5 mL). The mix was refluxed for 4 h under N2. The response was focused under decreased pressure, as well as the residue was extracted with diethylether; the organic stage was cleaned with brine, dried out over Na2Thus4 and focused under decreased pressure. The chemical substance was purified on florisil column chromatography (hexanes to 50% ethyl acetate in hexanes). Produce: 42%. 13C NMR (400 MHz, CDCl3) : 170.6, 151.7, 147.8, 143.7, 140.8, 133.6, 129.1, 122.9, 69.9, 21.5, 11.3, 9.1. 2.2.3. 17-(3-pyridyl)-5-androsta-16-ene-3-ol (5) Substance 4 (470 mg, 1.2 mmol) was dissolved in methanol (5 mL) at area temperature. A remedy of KOH (10%) in methanol (3.5 mL) was added, as well as the mix was stirred for 1.5 h, then focused under decreased pressure. Dichloromethane (25 mL) and drinking water (25 mL) had been added, as well as the mix was stirred for 1 h. The organic stage was dried out over Na2Thus4. The chemical substance was purified on florisil column chromatography (hexanes to 50% ethyl acetate in hexanes). Produce: 68%, purity 99.3% by HPLC. 1H NMR (400 MHz, CDCl3) : 8.6 (s, 1H), 8.4 (d, J = 4.8, 1H), 7.6 (d, J = 7.6, 1H), 7.2 (dd, J1 = 4.8 Hz and J2 = 7.6 Hz, 1H), 5.9 (d, J = 1.6 Hz), 4.0 (m, 1H), 2.2 (d, 1H), 2.0 (t, 2H), 1.2-1.8 (m, 17H), 0.9 (s, 3H), 0.8 (s, 3H). 13C NMR (400 MHz, CDCl3) : 151.5, 147.4, 147.3, 133.9, 133.1, 129.3, 123.1, 66.3, 57.5, 54.5, 47.5, 39.3, 36.2, 35.3, 34.0, 31.8, 31.7, 29.0, 28.4, 20.7, 16.7, 11.2. Assessed m/z for [M+H] = 352.2642 and predicted m/z = 352.2635. 2.2.4. 17-(3-pyridyl)- 5-androsta-16-ene-3-one (6) To a remedy of substance 5 (50 mg, 0.14 mmol) in acetone (4 mL), chromic acidity 10% (w/v) (4.5 mL) was drop-wise added at 0 C. The mix was stirred at area heat for 3 h, and a solution of sodium bicarbonate was then added to a pH = 7. The reaction combination was extracted with ethyl acetate, and the organic phase was washed with water and dried over Na2SO4. The compound was purified on silica gel column chromatography (hexanes to 40% ethyl acetate in hexanes). Yield: 30%, purity 99.4%. 1H NMR (400 MHz, CDCl3) : 8.6 (s, 1H), 8.4 (d, J = 4.8, 1H), 7.6 (d, J = 7.6, 1H), 7.2 (dd, J1 = 4.8 Hz and J2 = 7.6 Hz, 1H), 5.9 (d, J = 1.6 Hz), 2.4-1.2 (m, 20H), 1.1 (s, 3H), 1.0 (s, 3H). 13C NMR (400 MHz, CDCl3) : 211.8, 151.5, 147.4, 147.3, 134.2, 133.1, 129.3, 123.1, 66.3, 57.5, 54.5, 47.5, 39.3, 36.2, 35.3, 34.0, 31.8, 31.7, 29.0, 28.4, 20.7, 16.7, 11.2. Measured m/z for [M+H] = 350.2489 and predicted m/z = 350.2478. 2.2.5. 17-Iodoandrosta-5,16-dien-3-ol (9) Into a 100 mL round-bottomed flask, fitted with a magnetic stirring bar, was placed dehydroepiandrosterone (7) (1 g, 3.47 mmol) and ethanol (18 mL). Hydrazine hydrate answer (4.5 mL, 67.3 mmol) was added followed by a solution of hydrazine sulfate (0.05 g, 0.384 mmol) in water (0.5 mL). After stirring at room heat during 18 h, the combination was poured into cold water. The precipitate was collected by filtration and dried at room heat to yield the hydrazone 8 (96% yield). To a solution of compound 8 (2.3 g, 7.61 mmol) and triethylamine (9 mL, 64.82 mmol) in dioxane (42 mL) was added iodine (4.117 g, 16.22 mmol).