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

HRID 2397984Notes

Reaction equation

HRID 2397984 reaction equation
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH:9]=[C:10]4[C@:15]3([CH3:16])[CH:14]=[CH:13][C:12](=[O:20])[CH2:11]4)[C@@H:6]1[CH2:5][CH2:4][C:3]2=[O:21].[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@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH:9]=[C:10]4[C@:15]3([CH3:16])[CH:14]=[CH:13][C@H:12]([OH:20])[CH2:11]4)[C@@H:6]1[CH2:5][CH2:4][C@@H:3]2[OH:21]

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 572670321,5-Androstadiene-3,17-dione

Product 1

HCID 571202841,5-Androstadiene-3beta,17beta-diol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A tetrahydrofuran solution of the 1,5-androstadiene-3,17-dione so prepared is added to a solution of lithium tri-t-butoxyaluminum hydride in tetrahydrofuran. After stirring overnight at room temperature, 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 is dried over magnesium sulfate, the solvent removed and the residue is recrystallized from acetone to yield 1,5-androstadiene-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 is dried over magnesium sulfate
  5. customthe solvent removed
  6. customthe residue is recrystallized from acetone

Sources & evidence

ORD record
ord-9e36d7e2e4ef4f4482fa0a796e88e508
Source dataset
uspto-grants-1977_05
Patent number
US04022769

Reaction notes

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