Sodium Carbonate → Abiraterone Acetate

HRID 525308

Reaction equation

HRID 525308 reaction equation
O(C=C)S(C(F)(F)F)(=O)=O.[CH3:11][C:12]([O:14][C@@H:15]1[CH2:28][C:27]2[C@@:18]([CH3:34])([C@@H:19]3[C@@H:24]([CH2:25][CH:26]=2)[C@@H:23]2[CH2:29][CH2:30][C:31](=O)[C@@:22]2([CH3:33])[CH2:21][CH2:20]3)[CH2:17][CH2:16]1)=[O:13].C(B(CC)[C:38]1[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=1)C.FC(F)(F)S(OC1[C@]2(CC[C@H]3[C@@H](CC=C4[C@]3(C)CC[C@H](OC(=O)C)C4)[C@@H]2CC=1)C)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>O.C(OCC)(=O)C.O1CCCC1>[CH3:11][C:12]([O:14][C@@H:15]1[CH2:16][C:17]2[C@@:18]([CH3:34])([C@@H:19]3[C@@H:24]([CH2:25][CH:26]=2)[C@@H:23]2[CH2:29][CH:30]=[C:31]([C:42]4[CH:43]=[CH:38][CH:39]=[N:40][CH:41]=4)[C@@:22]2([CH3:33])[CH2:21][CH2:20]3)[CH2:27][CH2:28]1)=[O:13]

Participants

9

Reactant 5

HCID 10340Sodium CarbonateHCID 147093beta-Acetoxyandrost-5-en-17-oneHCID 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) acetateHCID 11769071Vinyl triflate2×

Product 1

HCID 9821849Abiraterone Acetate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The crude vinyl triflate thus obtained (about a 4:1 mixture of vinyl triflate and prasterone acetate) is taken up with tetrahydrofuran (3.7 L). Diethyl(3-pyridyl)borane (90 g), bis(triphenylphosphine)palladium II chloride (3.8 g) and a 2M sodium carbonate aqueous solution (1 L) are loaded under inert gas environment. The resulting mixture is refluxed for about 1 h, then cooled to room temperature, and ethyl acetate (2.5 L) and water (2.5 L) are added. The aqueous phase is back-extracted with ethyl acetate (1.4 L), the combined organic phases are treated with decolourising carbon (about 100 g), and then concentrated under vacuum to obtain crude abiraterone acetate as an oil (320 g; purity about 87%; assay 51%).

Workup

  1. temperatureThe resulting mixture is refluxed for about 1 h
  2. extractionThe aqueous phase is back-extracted with ethyl acetate (1.4 L)
  3. additionthe combined organic phases are treated with decolourising carbon (about 100 g)
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d7acb025435c4a3f91b314e9a17092be
Source dataset
uspto-grants-2016_05
Patent number
US09340571B2

Linked notes

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