Potassium sodium tartarate → 1alpha,7alpha-Dimethyl-androst-5-ene-3beta,17beta,19-triol 17,19-diacetate

HRID 1390765Notes

Reaction equation

HRID 1390765 reaction equation
[H-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].[C:19]([OH:22])(=[O:21])[CH3:20].[C:23]([OH:26])(=[O:25])[CH3:24].O[C@H:28]1[CH2:33][CH2:32][C@H:31]2[C@H:34]3[C@H:45]([CH2:46][CH2:47][C@:29]12[CH3:30])[C@:42]1([CH2:43]O)[C:37]([CH2:38][C:39](=[O:49])[CH2:40][C@@H:41]1[CH3:48])=[CH:36][C@H:35]3[CH3:50].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>O1CCCC1>[C:19]([O:22][C@H:28]1[CH2:33][CH2:32][C@H:31]2[C@H:34]3[C@H:45]([CH2:46][CH2:47][C@:29]12[CH3:30])[C@:42]1([CH2:43][O:25][C:23](=[O:26])[CH3:24])[C:37]([CH2:38][C@@H:39]([OH:49])[CH2:40][C@@H:41]1[CH3:48])=[CH:36][C@H:35]3[CH3:50])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 8673631317beta,19-Dihydroxy-1alpha,7alpha-dimethyl-5-androsten-3-one diacetate

Product 1

HCID 706048471alpha,7alpha-Dimethyl-androst-5-ene-3beta,17beta,19-triol 17,19-diacetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of lithium tri-t-butoxyaluminum hydride in tetrahydrofuran is added a tetrahydrofuran solution of 17β,19-dihydroxy-1α,7α-dimethyl-5-androsten-3-one diacetate. The resulting mixture is stirred at 20° C. for a period of 18 hours after which is added an aqueous solution of sodium potassium tartrate. The mixture is filtered and concentrated to a small volume under reduced pressure. The concentrate is taken up in ether and washed well with water. The combined ether extracts are dried over magnesium sulfate, filtered and the ether removed under vacuum to yield a residue which when crystallized from a mixture of acetone-hexane results in the preparation of the desired 1α,7α-dimethyl-androst-5-ene-3β,17β,19-triol 17,19-diacetate.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationconcentrated to a small volume under reduced pressure
  3. washwashed well with water
  4. dry with materialThe combined ether extracts are dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe ether removed under vacuum
  7. customto yield a residue which when
  8. customcrystallized from a mixture of acetone-hexane

Sources & evidence

ORD record
ord-47a33a8abc4c4c639df298787077c525
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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