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

HRID 1733109Notes

Reaction equation

HRID 1733109 reaction equation
[CH3:1][C@H:2]1[C@@:19]2([CH3:20])[C:6](=[CH:7][CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C:13]2=[O:21])[CH2:5][C:4](=[O:22])[CH2:3]1.[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>[CH3:1][C@H:2]1[C@@:19]2([CH3:20])[C:6](=[CH:7][CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[OH:21])[CH2:5][C@@H:4]([OH:22])[CH2:3]1

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 705847521beta-Methyl-5-androstene-3,17-dione

Product 1

HCID 705848031beta-Methyl-5-androstene-3beta,17beta-diol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A tetrahydrofuran solution of 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 a period of 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 is crystallized from an acetone-hexane solution to yield 1β-methyl-5-androstene-3β,17β-diol.

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 is crystallized from an acetone-hexane solution

Sources & evidence

ORD record
ord-8644ee7d221a4896ba1c1559bd1afd39
Source dataset
uspto-grants-1980_12
Patent number
US04239681

Reaction notes

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