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

HRID 1834934Notes

Reaction equation

HRID 1834934 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-e6f8de74eb204f7db1c0d8100f39a762
Source dataset
uspto-grants-1978_01
Patent number
US04071624

Reaction notes

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