Potassium sodium tartarate → HCID 22806882, compound

HRID 1390782Notes

Reaction equation

HRID 1390782 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@@H:19]([O:25][C:26]3([O:32][CH3:33])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[CH2:18][CH2:17]4)[CH2:14][CH:13]=[C:12]1[CH2:11][C:10](=[O:34])[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.[Na+].[K+]>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]([O:25][C:26]3([O:32][CH3:33])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]3)[CH2:18][CH2:17]4)[CH2:14][CH:13]=[C:12]1[CH2:11][C@@H:10]([OH:34])[CH2:9][CH2:8]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 86736322HCID 86736322, compound

Product 1

HCID 22806882HCID 22806882, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A tetrahydrofuran solution of 19-hydroxy-17β-(1'-methoxycyclohexyloxy)androst-5-en-3-one acetate is added under nitrogen to a solution of lithium tri-t-butoxyaluminum hydride in tetrahydrofuran. After stirring at room temperature overnight, 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 and the solvent removed. The residue which remains is recrystallized from acetone to yield 17β-(1'-methoxycyclohexyloxy)-5-androstene-3β,19-diol 19-acetate.

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
  6. customThe residue which remains is recrystallized from acetone

Sources & evidence

ORD record
ord-9111e5375b8848c593696cda37a1727f
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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