Ammonium Chloride → 17beta,19-Dihydroxy-7alpha-methyl-5-androsten-3-one

HRID 1390752Notes

Reaction equation

HRID 1390752 reaction equation
CC(C)([O-])C.[K+].[OH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]2[C@H:14]3[C@H:25]([CH2:26][CH2:27][C@:9]12[CH3:10])[C@:22]1([CH2:23][OH:24])[C:17](=[CH:18][C:19](=[O:28])[CH2:20][CH2:21]1)[CH2:16][C@H:15]3[CH3:29].[Cl-].[NH4+]>CS(C)=O>[OH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]2[C@H:14]3[C@H:25]([CH2:26][CH2:27][C@:9]12[CH3:10])[C@:22]1([CH2:23][OH:24])[C:17]([CH2:18][C:19](=[O:28])[CH2:20][CH2:21]1)=[CH:16][C@H:15]3[CH3:29]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 7058499517beta,19-Dihydroxy-7alpha-methyl-4-androstene-3-one

Product 1

HCID 7060530117beta,19-Dihydroxy-7alpha-methyl-5-androsten-3-one

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 a solution of 17β,19-dihydroxy-7α-methyl-4-androsten-3-one in dimethylsulfoxide. After standing for 15 minutes, the mixture is poured onto a cold aqueous ammonium chloride solution. The solid which forms is rapidly filtered, washed well with water and dissolved in ether. The ether solution is washed well with water and dried over sodium sulfate. The ether is removed at room temperature to yield 17β,19-dihydroxy-7α-methyl-5-androsten-3-one.

Workup

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

Sources & evidence

ORD record
ord-1e49cf2cd2524e44accc68ba9f564e95
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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