HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → Anhydro abiraterone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 3-(Diethylboryl)pyridine | HCID 642851 | — |
| Reactant | [(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 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Anhydro abiraterone | HCID 10314660 | 84% |
Reaction Steps
The method followed that described in Example 1, using in step (b) diethyl(3-pyridyl)borane (0.88 g, 6.0 mmol), androsta-3,5,16-trien-17-yl trifluoromethanesulphonate (2.01 g, 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 δ1.02(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-H), 8.63(1H,m,Py 2-H); MS m/z 331 (M+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05604213 |
| Source dataset | uspto-grants-1997_02 |
| ORD ID | ord-a6a53953e8794a9abbbf47c6f41773be |
| Source note | uspto-grants-1997_02 |