Potassium sodium tartarate → 1alpha-Methyl-5-androstene-3beta,17beta,19-triol

HRID 1390734Notes

Reaction equation

HRID 1390734 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:19]([CH2:20][CH2:21][C@:3]12[CH3:4])[C@:16]1([CH2:17][OH:18])[C:11]([CH2:12][C:13](=[O:23])[CH2:14][C@@H:15]1[CH3:22])=[CH:10][CH2:9]3.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>O1CCCC1>[CH3:22][C@@H:15]1[C@@:16]2([CH2:17][OH:18])[C:11](=[CH:10][CH2:9][C@@H:8]3[C@@H:19]2[CH2:20][CH2:21][C@@:3]2([CH3:4])[C@H:5]3[CH2:6][CH2:7][C@@H:2]2[OH:1])[CH2:12][C@@H:13]([OH:23])[CH2:14]1

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 7060471217beta,19-Dihydroxy-1alpha-methyl-5-androsten-3-one

Product 1

HCID 706054601alpha-Methyl-5-androstene-3beta,17beta,19-triol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 17β,19-dihydroxy-1α-methyl-5-androsten-3-one in tetrahydrofuran is added to a suspension of lithium aluminum hydride in tetrahydrofuran. After stirring overnight at room temperature an aqueous solution of sodium potassium tartrate is added until a readily filtered granular precipitate forms. This precipitate is removed by filtration and washed well with ether. The filtrate and ether washings are combined, washed with water, dried over magnesium sulfate and concentrated under vacuum. Crystallization of the residue yields 1α-methyl-5-androstene-3β,17β,19-triol.

Workup

  1. additionis added until a readily filtered granular precipitate forms
  2. customThis precipitate is removed by filtration
  3. washwashed well with ether
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. customCrystallization of the residue

Sources & evidence

ORD record
ord-ff94e25111c54368b78269d5f6333f61
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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