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

HRID 2397991Notes

Reaction equation

HRID 2397991 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 so prepared 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 from the filtrate. The residue which is crystallized from acetone-hexane yields 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 from the filtrate
  6. customThe residue which is crystallized from acetone-hexane

Sources & evidence

ORD record
ord-5ac841969b834defaa537c7b2760291a
Source dataset
uspto-grants-1977_05
Patent number
US04022769

Reaction notes

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