Hydrochloric Acid → Pregna-5,7-dien-21-ol

HRID 1587606Notes

Reaction equation

HRID 1587606 reaction equation
COC(O[C@@H:6]1[C@@:26]2([CH3:27])[C:10](=[CH:11][CH:12]=[C:13]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:28])[C@H:14]3[CH2:15][CH2:16][C@@H:17]2[CH:18]([CH:20]=[O:21])C)[CH2:9][C@@H:8](OC(OC)=O)[CH2:7]1)=O.[BH4-].[Na+].Cl>C(O)C.O>[CH2:20]([OH:21])[CH2:18][C@@H:17]1[C@:22]2([CH3:28])[C@H:14]([C:13]3[C@H:25]([CH2:24][CH2:23]2)[C@:26]2([CH3:27])[C:10]([CH2:9][CH2:8][CH2:7][CH2:6]2)=[CH:11][CH:12]=3)[CH2:15][CH2:16]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 543675231alpha,3beta-Bis(methoxycarbonyloxy)pregna-5,7-diene-20-carbaldehyde

Product 1

HCID 131717975Pregna-5,7-dien-21-ol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In 2 ml of ethanol was dissolved 100 mg of 1α,3β-bis(methoxycarbonyloxy)pregna-5,7-diene-20-carbaldehyde . Then, under ice-cooling, 20 mg of sodium borohydride was added and the reaction mixture was stirred for 30 minutes. The reaction mixture was neutralized with diluted hydrochloric acid under ice-cooling and, after diluted with water, extracted with diethyl ether. The extract was serially washed with aqueous sodium hydrogen carbonate solution and aqueous sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 83 mg of 20-methyl-1α,3β-bis)methoxycarbonyloxy)pregna-5,7-dien-21-ol.

Workup

  1. temperatureThen, under ice-cooling
  2. temperaturecooling
  3. extractionextracted with diethyl ether
  4. washThe extract was serially washed with aqueous sodium hydrogen carbonate solution and aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-14ac1bf680414ba18621b09738973935
Source dataset
uspto-grants-1993_06
Patent number
US05218109

Reaction notes

Loading…