Potassium sodium tartarate → 19-Trimethylsiloxy-5-androstene-3beta,17beta-diol

HRID 1390780Notes

Reaction equation

HRID 1390780 reaction equation
[CH3:1][Si:2]([CH3:26])([CH3:25])[O:3][CH2:4][C@@:5]12[C@@H:22]3[C@H:13]([C@H:14]4[C@@:18]([CH2:20][CH2:21]3)([CH3:19])[C:17](=[O:23])[CH2:16][CH2:15]4)[CH2:12][CH:11]=[C:10]1[CH2:9][C:8](=[O:24])[CH2:7][CH2:6]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>O1CCCC1>[CH3:25][Si:2]([CH3:1])([CH3:26])[O:3][CH2:4][C@@:5]12[C@@H:22]3[C@H:13]([C@H:14]4[C@@:18]([CH2:20][CH2:21]3)([CH3:19])[C@@H:17]([OH:23])[CH2:16][CH2:15]4)[CH2:12][CH:11]=[C:10]1[CH2:9][C@@H:8]([OH:24])[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 2280690519-Trimethylsiloxy-5-androstene-3,17-dione

Product 1

HCID 2280686219-Trimethylsiloxy-5-androstene-3beta,17beta-diol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A tetrahydrofuran solution of 19-trimethylsiloxy-5-androstene-3,17-dione is added to lithium aluminum hydride in tetrahydrofuran and the resultant solution stirred overnight at room temperature. An aqueous solution of sodium potassium tartrate is added with stirring until a readily filterable precipitate forms. The filtrate is concentrated under reduced pressure and diluted with ether. The resulting solution is washed with water, dried over magnesium sulfate, and the ether removed under vacuum. The residual 19-trimethylsiloxy-5-androstene-3β,17β-diol so obtained is recrystallized from an acetone-hexane solution.

Workup

  1. concentrationThe filtrate is concentrated under reduced pressure
  2. additiondiluted with ether
  3. washThe resulting solution is washed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe ether removed under vacuum

Sources & evidence

ORD record
ord-df1534513b1f413dac54fe117c241b5f
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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