Potassium sodium tartarate → HCID 70585967, compound

HRID 371819Notes

Reaction equation

HRID 371819 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](=[CH:38][C:39](=[O:48])[CH2:40][CH2:41]1)[CH2:36][CH2:35]3.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](=[CH:38][C@@H:39]([OH:48])[CH2:40][CH2:41]1)[CH2:36][CH2:35]3)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 86734741HCID 86734741, compound

Product 1

HCID 70585967HCID 70585967, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of lithium tri-t-butoxy-aluminum hydride in tetrahydrofuran is added a tetrahydrofuran solution of 17β,19-dihydroxyandrost-4-en-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 recrystallized from a mixture of acetone-hexane results in the preparation of the desired androst-4-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. customrecrystallized from a mixture of acetone-hexane

Sources & evidence

ORD record
ord-83f758f987634d2e8286ec7910f427e8
Source dataset
uspto-grants-1978_05
Patent number
US04087524

Reaction notes

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