Potassium sodium tartarate → 1beta-Methyl-5-androstene-3beta,17beta,19-triol

HRID 1390742Notes

Reaction equation

HRID 1390742 reaction equation
[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][CH:9]=[C:8]1[CH2:7][C:6](=[O:22])[CH2:5][C@H:4]2[CH3:23].[H-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>O1CCCC1>[CH3:23][C@H:4]1[C@@:3]2([CH2:2][OH:1])[C:8](=[CH:9][CH2:10][C@@H:11]3[C@@H:20]2[CH2:19][CH2:18][C@@:16]2([CH3:17])[C@H:12]3[CH2:13][CH2:14][C@@H:15]2[OH:21])[CH2:7][C@@H:6]([OH:22])[CH2:5]1

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 7060652019-Hydroxy-1beta-methyl-5-androstene-3,17-dione

Product 1

HCID 706047781beta-Methyl-5-androstene-3beta,17beta,19-triol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A tetrahydrofuran solution of 19-hydroxy-1β-methyl-5-androstene-3,17-dione is added under nitrogen to a solution of lithium tri-t-butoxyaluminum hydride in tetrahydrofuran. After stirring at room temperature for about 18 hours, an aqueous solution of potassium sodium tartrate is added with stirring to form a readily filterable white solid. The reaction mixture is filtered, the filtrate dried over magnesium sulfate, and the solvent removed. The residue which remains is crystallized from an acetone-hexane solution to yield 1β-methyl-5-androstene-3β,17β,19-triol.

Workup

  1. stirringwith stirring
  2. customto form a readily filterable white solid
  3. filtrationThe reaction mixture is filtered
  4. dry with materialthe filtrate dried over magnesium sulfate
  5. customthe solvent removed
  6. customThe residue which remains is crystallized from an acetone-hexane solution

Sources & evidence

ORD record
ord-e1b5303a627d4ea2ba6962b7c113240c
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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