Potassium sodium tartarate → HCID 70585967, compound

HRID 2398006Notes

Reaction equation

HRID 2398006 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×

Procedure

To a solution of lithium tri-t-butoxyaluminum hydride in tetrahydrofuran is added a tetrahydrofuran solution of 17β,19-dihydroxy-4-androsten-3-one diacetate. The resulting mixture is stirred at 20° C. for a period of about 18 hours after which an aqueous solution of sodium potassium tartrate is added. 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 ether solution is dried over magnesium sulfate, filtered and the ether removed under vacuum to yield a residue which is crystallized from acetone-hexane to yield androst-4-ene-3β,17β,19-triol 17,19-diacetate.

Workup

  1. additionis added
  2. filtrationThe mixture is filtered
  3. concentrationconcentrated to a small volume under reduced pressure
  4. washwashed well with water
  5. dry with materialThe ether solution is dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe ether removed under vacuum
  8. customto yield a residue which
  9. customis crystallized from acetone-hexane

Sources & evidence

ORD record
ord-c196ef3ece2c4723bf973cdc07a0a3c0
Source dataset
uspto-grants-1977_05
Patent number
US04022769

Reaction notes

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