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

HRID 1834927Notes

Reaction equation

HRID 1834927 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-98feea5ec3b6487ebf62a20b2d7ce935
Source dataset
uspto-grants-1978_01
Patent number
US04071624

Reaction notes

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