Dipotassium 2,3-dihydroxybutanedioate → 19-Tetrahydropyranyloxy-1,5-androstadiene-3beta,17beta-diol

HRID 1390737Notes

Reaction equation

HRID 1390737 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C@@:9]12[C@@H:26]3[C@H:17]([C@H:18]4[C@@:22]([CH2:24][CH2:25]3)([CH3:23])[C:21](=[O:27])[CH2:20][CH2:19]4)[CH2:16][CH:15]=[C:14]1[CH2:13][C:12](=[O:28])[CH:11]=[CH:10]2.[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.[K+].[K+]>O1CCCC1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C@@:9]12[C@@H:26]3[C@H:17]([C@H:18]4[C@@:22]([CH2:24][CH2:25]3)([CH3:23])[C@@H:21]([OH:27])[CH2:20][CH2:19]4)[CH2:16][CH:15]=[C:14]1[CH2:13][C@@H:12]([OH:28])[CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 6100505Dipotassium 2,3-dihydroxybutanedioateHCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 2280690219-Tetrahydropyranyloxy-1,5-androstadiene-3,17-dione

Product 1

HCID 2280690319-Tetrahydropyranyloxy-1,5-androstadiene-3beta,17beta-diol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A tetrahydrofuran solution of 19-tetrahydropyranyloxy-1,5-androstadiene-3,17-dione is added under nitrogen to a solution of lithium tri-t-butoxyaluminum hydride in tetrahydrofuran. After stirring overnight at room temperature, an aqueous solution of potassium 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 by evaporation. The residue which remains is crystallized from an acetone solution to yield 19-tetrahydropyranyloxy-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 by evaporation
  6. customThe residue which remains is crystallized from an acetone solution

Sources & evidence

ORD record
ord-ae27a436963a44bd931b8437c65ace27
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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