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

HRID 1834973Notes

Reaction equation

HRID 1834973 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 to a solution of lithium tri-t-butoxyaluminum hydride in tetrahydrofuran under nitrogen. 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 and the filtrate dried over magnesium sulfate. The solvent is removed and the residue 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 is removed
  6. customthe residue recrystallized from acetone

Sources & evidence

ORD record
ord-edd89f60d83f49108fed65ebdb3b6086
Source dataset
uspto-grants-1978_01
Patent number
US04071625

Reaction notes

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