Potassium sodium tartarate → HCID 70614875, compound

HRID 1834959Notes

Reaction equation

HRID 1834959 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([OH:8])(=[O:7])[CH3:6].O[C@H:10]1[CH2:27][CH2:26][C@@:25]2([CH2:28]O)[C@@H:12]([CH2:13][CH2:14][C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@H:16]3[CH2:17][CH2:18][C:19]2=[O:30])[CH2:11]1.[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][C@H:10]1[CH2:27][CH2:26][C@@:25]2([CH2:28][O:7][C:5](=[O:8])[CH3:6])[C@@H:12]([CH2:13][CH2:14][C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[OH:30])[CH2:11]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 86735423HCID 86735423, compound

Product 1

HCID 70614875HCID 70614875, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A tetrahydrofuran solution of 3β,19-dihydroxy-5α-androstan-17-one diacetate is added to lithium tri-t-butoxyaluminum hydride in tetrahydrofuran and the resultant solution stirred overnight at room temperature. Aqueous 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 5α-androstane-3β,17β,19-triol 3,19-diacetate is crystallized from an acetone-hexane solution.

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 5α-androstane-3β,17β,19-triol 3,19-diacetate is crystallized from an acetone-hexane solution

Sources & evidence

ORD record
ord-1e640ed554fb452faf9a12eff599cf1e
Source dataset
uspto-grants-1978_01
Patent number
US04071625

Reaction notes

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