Potassium sodium tartarate → HCID 70584930, compound

HRID 1834951Notes

Reaction equation

HRID 1834951 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].O[CH2:6][C@@:7]12[C@@H:24]3[C@H:15]([C@H:16]4[C@@:20]([CH2:22][CH2:23]3)([CH3:21])[C:19](=[O:25])[CH2:18][CH2:17]4)[CH2:14][CH2:13][C:12]1=[CH:11][C:10](=[O:26])[CH2:9][CH2:8]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+].[Na+]>O1CCCC1>[C:1]([O:4][CH2:6][C@@:7]12[C@@H:24]3[C@H:15]([C@H:16]4[C@@:20]([CH2:22][CH2:23]3)([CH3:21])[C@@H:19]([OH:25])[CH2:18][CH2:17]4)[CH2:14][CH2:13][C:12]1=[CH:11][C@@H:10]([OH:26])[CH2:9][CH2:8]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 86734750HCID 86734750, compound

Product 1

HCID 70584930HCID 70584930, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A tetrahydrofuran solution of 19-hydroxy-4-androstene-3,17-dione acetate is added to lithium tri-t-butoxy-aluminum hydride in tetrahydrofuran, and the resultant solution stirred overnight at room temperature. An aqueous solution of sodium potassium tartrate is added with stirring until a readily filterable precipitate forms. The filtrate is concentrated under reduced pressure and diluted with ether. The resulting solution is washed with water, dried over magnesium sulfate and the ether removed under vacuum. The residual androst-4-ene-3β,17β,19-triol 19-acetate is crystallized from acetone.

Workup

  1. concentrationThe filtrate is concentrated under reduced pressure
  2. additiondiluted with ether
  3. washThe resulting solution is washed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe ether removed under vacuum
  6. customThe residual androst-4-ene-3β,17β,19-triol 19-acetate is crystallized from acetone

Sources & evidence

ORD record
ord-3d5e8cb6ffed4bc784567732cd510011
Source dataset
uspto-grants-1978_01
Patent number
US04071624

Reaction notes

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