Hydrochloric Acid → Abiraterone

HRID 1451361Notes

Reaction equation

HRID 1451361 reaction equation
C([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH:13]=[C:14]2[C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH2:6]1)(=O)C.[OH-].[Na+].Cl.C(=O)(O)[O-].[Na+]>CO.O>[N:26]1[CH:27]=[CH:28][CH:29]=[C:24]([C:14]2[C@:15]3([CH2:17][CH2:18][C@H:19]4[C@@H:10]([CH2:9][CH:8]=[C:7]5[C@:20]4([CH3:23])[CH2:21][CH2:22][C@H:5]([OH:4])[CH2:6]5)[C@@H:11]3[CH2:12][CH:13]=2)[CH3:16])[CH:25]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 9821849Abiraterone Acetate

Product 1

HCID 132971AbirateroneYield 79%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3β-acetoxy-17-(3-pyridyl)androsta-5,16-diene (4.90 g, 12.5 mmol) in methanol (50 ml) was added an aqueous solution of sodium hydroxide (10% w/v, 10 ml) and the mixture heated, with stirring, on an oil bath at 80° C. for 5 min., then allowed to cool. The mixture was poured into water, neutralised with hydrochloric acid (1M), rebasified with saturated sodium bicarbonate solution, and extracted with hot toluene (3×100 ml). The toluene extracts were combined, dried (Na2CO3), and concentrated. Chromatography, on elution with toluene-diethyl ether (2:1) afforded the title compound (3.45 g, 79%) which crystallised from toluene, mp 228°-229° C.; 1H-NMR (CDCl3 inter alia δ1.05(3H,s,19-CH3), 1.07(3H,s,18-CH3), 3.54(1H,m,3α-H), (5.40H,dm,J 5.0 Hz, 6-H), 5.99(1H,m,16-H), 7.22(1H,m,Py5-H), 7.65(1H,m,Py 4-H), 8.46(1H,m,Py 6-H), 8.62(1H,m,Py 2-H). Anal. Calcd: C, 82.47; H, 8.94; N, 4.01. Found: C, 82.40; H, 8.91; N, 3.97%.

Workup

  1. temperaturethe mixture heated
  2. temperatureto cool
  3. extractionextracted with hot toluene (3×100 ml)
  4. dry with materialdried (Na2CO3)
  5. concentrationconcentrated
  6. washChromatography, on elution with toluene-diethyl ether (2:1)

Sources & evidence

ORD record
ord-9d91f6429fbb451bb5d5d9cf1e131b6d
Source dataset
uspto-grants-1997_02
Patent number
US05604213

Reaction notes

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