Ammonium Chloride → 19-Hydroxy-1beta-methyl-5-androstene-3,17-dione

HRID 1390741Notes

Reaction equation

HRID 1390741 reaction equation
CC(C)([O-])C.[K+].[OH:7][CH2:8][C@@:9]12[C@@H:26]3[C@H:17]([C@H:18]4[C@@:22]([CH2:24][CH2:25]3)([CH3:23])[C:21](=[O:27])[CH2:20][CH2:19]4)[CH2:16][CH2:15][C:14]1=[CH:13][C:12](=[O:28])[CH2:11][C@H:10]2[CH3:29].[Cl-].[NH4+]>CS(C)=O>[OH:7][CH2:8][C@@:9]12[C@@H:26]3[C@H:17]([C@H:18]4[C@@:22]([CH2:24][CH2:25]3)([CH3:23])[C:21](=[O:27])[CH2:20][CH2:19]4)[CH2:16][CH:15]=[C:14]1[CH2:13][C:12](=[O:28])[CH2:11][C@H:10]2[CH3:29]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 5427936919-Hydroxy-1beta-methyl-4-androsten-3,17-dione

Product 1

HCID 7060652019-Hydroxy-1beta-methyl-5-androstene-3,17-dione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of potassium t-butoxide in dimethylsulfoxide at 25° C. under nitrogen is added with stirring 19-hydroxy-1β-methyl-4-androstene-3,17-dione in dimethylsulfoxide. After 15 minutes the mixture is poured onto a cold aqueous ammonium chloride solution. The solid is rapidly filtered, washed well with water and dissolved in ether. The ether solution is again washed with water and dried over sodium sulfate. The ether is removed at room temperature to yield 19-hydroxy-1β-methyl-5-androstene-3,17-dione.

Workup

  1. filtrationThe solid is rapidly filtered
  2. washwashed well with water
  3. dissolutiondissolved in ether
  4. washThe ether solution is again washed with water
  5. dry with materialdried over sodium sulfate
  6. customThe ether is removed at room temperature

Sources & evidence

ORD record
ord-3eabafddfbe5472496586451cd8416ff
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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