Sodium Carbonate → Abiraterone

HRID 53189

Reaction equation

HRID 53189 reaction equation
C(B(CC)[C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)C.I[C:13]1[C@:14]2([CH2:31][CH2:30][C@H:29]3[C@@H:19]([CH2:20][CH:21]=[C:22]4[C@:27]3([CH3:28])[CH2:26][CH2:25][C@H:24]([OH:32])[CH2:23]4)[C@@H:16]2[CH2:17][CH:18]=1)[CH3:15].C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([C:13]2[C@:14]3([CH2:31][CH2:30][C@H:29]4[C@@H:19]([CH2:20][CH:21]=[C:22]5[C@:27]4([CH3:28])[CH2:26][CH2:25][C@H:24]([OH:32])[CH2:23]5)[C@@H:16]3[CH2:17][CH:18]=2)[CH3:15])[CH:5]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 6428513-(Diethylboryl)pyridineHCID 11069352(3S,8R,9S,10R,13S,14S)-17-iodo-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta(a)phenanthren-3-ol

Product 1

HCID 132971Abiraterone

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Diethyl(3-pyridyl)borane (3.23 g, 22 mmol) from Aldrich Chemical Co. Ltd. was added to a stirred solution of 17-iodo-androsta-5,16-dien-3β-ol (7.96 g, 20 mmol) in THF (120 ml) containing bis(triphenylphosphine)palladium (II) chloride (140 mg, 0.2 mmol). An aqueous solution of sodium carbonate (2M, 50 ml) was then added and the mixture heated, with stirring, by an oil bath at 80° C. for 48 h, and allowed to cool.

Workup

  1. temperaturethe mixture heated
  2. temperatureto cool

Sources & evidence

ORD record
ord-ec36e245e4bc42cbbd4e9cfcb89b3272
Source dataset
uspto-grants-1997_04
Patent number
US05618807

Linked notes

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