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Sodium Carbonate → Anhydro abiraterone
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Sodium Carbonate | HCID 10340 | — |
| 反応物 | 3-(Diethylboryl)pyridine | HCID 642851 | — |
| 反応物 | [(8R,9S,10R,13S,14S)-10,13-dimethyl-2,7,8,9,11,12,14,15-octahydro-1H-cyclopenta[a]phenanthren-17-yl] trifluoromethanesulfonate | HCID 10476216 | — |
| 触媒 | HCID 178418476 | HCID 178418476 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | Anhydro abiraterone | HCID 10314660 | 84% |
反応手順
The method followed that described in Example 1, using in step (b) diethyl(3-pyridyl)borane (0.88g, 6.0 mmol), androsta-3,5,16-trien-17-yl trifluoromethanesulphonate (2.01g, 5.0 mmol), prepared in step (a), THF (25 ml), bis(triphenylphosphine)palladium(II) chloride (35 mg, 0.05 mmol), and aqueous sodium carbonate (2M, 10 ml). Chromatography, on elution with dichloromethane, afforded the title compound (1.39 g, 84%) which crystallised from hexane, m.p. 110°-112° C. 1H-NMR (CDCl3) inter alia δ 1.02(3H,s,19-CH3), 1.07(3H,s,18-CH3), 5.44(1H,m,6-H), 5.61(1H,m,3-H), 5.95(1H,dm, J 9.8 Hz, 4-H), 6.01(1H,m, 16-H), 7.23(1H,m,Py 5-H), 7.66(1H,m,Py 4-H), 8.46(1H,m,Py 6-hr), 8.63(1H,m,Py 2-H); MS m/z 331 (M+).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05618807 |
| 出典データセット | uspto-grants-1997_04 |
| ORD ID | ord-4a2ce9feb87d4d10bdd8e66b84826df9 |
| 出典メモ | uspto-grants-1997_04 |