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

HRID 1733104Notes

Reaction equation

HRID 1733104 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 1,5-androstadiene-3,17-dione is added under nitrogen to a solution of lithium tri-t-butoxyaluminum hydride in tetrahydrofuran. After stirring at room temperature overnight, an aqueous solution of potassium sodium tartrate is added with stirring to form a readily filterable white solid. The reaction mixture is filtered and the filtrate dried over magnesium sulfate and the solvent removed. The residue which remains 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 dried over magnesium sulfate
  5. customthe solvent removed
  6. customThe residue which remains is recrystallized from acetone

Sources & evidence

ORD record
ord-816e707e87c842178e37fc357b182e2b
Source dataset
uspto-grants-1980_12
Patent number
US04239681

Reaction notes

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