3-(Diethylboryl)pyridine → Abiraterone Acetate

HRID 525307Notes

Reaction equation

HRID 525307 reaction equation
FC(F)(F)S(O[C:7]1[C@:8]2([CH2:25][CH2:24][C@H:23]3[C@@H:13]([CH2:14][CH:15]=[C:16]4[C@:21]3([CH3:22])[CH2:20][CH2:19][C@H:18]([O:26][C:27](=[O:29])[CH3:28])[CH2:17]4)[C@@H:10]2[CH2:11][CH:12]=1)[CH3:9])(=O)=O.C(B(CC)[C:35]1[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=1)C>>[CH3:28][C:27]([O:26][C@@H:18]1[CH2:17][C:16]2[C@@:21]([CH3:22])([C@@H:23]3[C@@H:13]([CH2:14][CH:15]=2)[C@@H:10]2[CH2:11][CH:12]=[C:7]([C:39]4[CH:40]=[CH:35][CH:36]=[N:37][CH:38]=4)[C@@:8]2([CH3:9])[CH2:25][CH2:24]3)[CH2:20][CH2:19]1)=[O:29]

Participants

3

Reactant 2

HCID 6428513-(Diethylboryl)pyridineHCID 10457059((3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-(trifluoromethylsulfonyloxy)-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta(a)phenanthren-3-yl) acetate

Product 1

HCID 9821849Abiraterone Acetate

Procedure

The Suzuki reaction between 3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate (II) and diethyl(3-pyridyl)borane affords crude abiraterone acetate which is purified by silica gel chromatography, eluting with a mixture of ethyl ether and petroleum ether, and finally crystallised from hexane.

Sources & evidence

ORD record
ord-6bad42bc2af8438bbf7cc845c0ea09b4
Source dataset
uspto-grants-2016_05
Patent number
US09340571B2

Reaction notes

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