Sodium Carbonate → Anhydro abiraterone

HRID 53181Notes

Reaction equation

HRID 53181 reaction equation
C(B(CC)[C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)C.FC(F)(F)S(O[C:18]1[C@:19]2([CH2:36][CH2:35][C@H:34]3[C@@H:24]([CH2:25][CH:26]=[C:27]4[C@:32]3([CH3:33])[CH2:31][CH2:30][CH:29]=[CH:28]4)[C@@H:21]2[CH2:22][CH:23]=1)[CH3:20])(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([C:18]2[C@:19]3([CH2:36][CH2:35][C@H:34]4[C@@H:24]([CH2:25][CH:26]=[C:27]5[C@:32]4([CH3:33])[CH2:31][CH2:30][CH:29]=[CH:28]5)[C@@H:21]3[CH2:22][CH:23]=2)[CH3:20])[CH:5]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 6428513-(Diethylboryl)pyridineHCID 10476216[(8R,9S,10R,13S,14S)-10,13-dimethyl-2,7,8,9,11,12,14,15-octahydro-1H-cyclopenta[a]phenanthren-17-yl] trifluoromethanesulfonate

Product 1

HCID 10314660Anhydro abirateroneYield 84%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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+).

Workup

  1. washChromatography, on elution with dichloromethane

Sources & evidence

ORD record
ord-4a2ce9feb87d4d10bdd8e66b84826df9
Source dataset
uspto-grants-1997_04
Patent number
US05618807

Reaction notes

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