Sodium Carbonate → Anhydro abiraterone

HRID 53181노트

반응식

HRID 53181 반응식
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

참가 물질

6

반응물 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

생성물 1

HCID 10314660Anhydro abiraterone수율 84%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

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+).

후처리

  1. washChromatography, on elution with dichloromethane

출처 및 근거

ORD 기록
ord-4a2ce9feb87d4d10bdd8e66b84826df9
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05618807

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