Hydrochloric Acid → HCID 11163742, compound

HRID 382846Notes

Reaction equation

HRID 382846 reaction equation
C(O)C.[OH:4][C@@H:5]1[CH2:25][C:24]2[C@:19]([CH3:27])([CH:20]=[CH:21][C:22](=[O:26])[CH:23]=2)[C@@H:18]2[C@@H:6]1[C@H:7]1[C@:15]([CH3:28])([CH2:16][CH2:17]2)[C@@H:10]([C@@H:11]([CH:13]=[O:14])[CH3:12])[CH2:9][CH2:8]1.[BH4-].[Na+].Cl>O>[OH:4][C@@H:5]1[CH2:25][C:24]2[C@:19]([CH3:27])([CH:20]=[CH:21][C:22](=[O:26])[CH:23]=2)[C@@H:18]2[C@@H:6]1[C@H:7]1[C@:15]([CH3:28])([CH2:16][CH2:17]2)[C@@H:10]([C@H:11]([CH3:12])[CH2:13][OH:14])[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 4311764Sodium borohydrideHCID 15485230HCID 15485230, compound

Product 1

HCID 11163742HCID 11163742, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethanol (200 ml) was added to 20.0 g of (7α,20S)-7-hydroxy-3-oxo-pregna-1,4-diene-20-carbaldehyde. To this solution was added 0.61 g of sodium borohydride in several portions with stirring under ice cooling. After completion of the addition, the mixture was further stirred for 1 hour under ice cooling. The reaction mixture was neutralized with 1 N hydrochloric acid, then 200 ml of water was added, and the ethanol was distilled off under reduced pressure. The precipitate was collected by filtration, washed with water, then dehydrated by adding toluene to the precipitate and removing water by azeotropic distillation, and concentrated to give 18.8 g of (7α,20S)-7,21-dihydroxy-20-methyl-pregna-1,4-dien-3-one (yield 93%).

Workup

  1. additionAfter completion of the addition
  2. stirringthe mixture was further stirred for 1 hour under ice cooling
  3. distillationthe ethanol was distilled off under reduced pressure
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. additionby adding toluene to the precipitate
  7. customremoving water
  8. distillationby azeotropic distillation
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-3eb4a9972ae043a4b479db526c3f5634
Source dataset
uspto-grants-2001_10
Patent number
US06310225B1

Reaction notes

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