Hydrochloric Acid → (7alpha,20S)-7,21-Dihydroxy-20-methylpregn-4-en-3-one

HRID 860846Notes

Reaction equation

HRID 860846 reaction equation
[OH:1][C@@H:2]1[CH2:22][C:21]2[C@:16]([CH3:24])([CH2:17][CH2:18][C:19](=[O:23])[CH:20]=2)[C@@H:15]2[C@@H:3]1[C@H:4]1[C@:12]([CH3:25])([CH2:13][CH2:14]2)[C@@H:7]([C@@H:8]([CH:10]=[O:11])[CH3:9])[CH2:6][CH2:5]1.[BH4-].[Na+].Cl>C(O)C>[OH:1][C@@H:2]1[CH2:22][C:21]2[C@:16]([CH3:24])([CH2:17][CH2:18][C:19](=[O:23])[CH:20]=2)[C@@H:15]2[C@@H:3]1[C@H:4]1[C@:12]([CH3:25])([CH2:13][CH2:14]2)[C@@H:7]([C@H:8]([CH3:9])[CH2:10][OH:11])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 87708869(20s)-7alpha-Hydroxy-pregn-4-en-3-one-20-carbaldehyde

Product 1

HCID 11175416(7alpha,20S)-7,21-Dihydroxy-20-methylpregn-4-en-3-oneYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Ethanol (20 ml) was added to (20S)-7α-hydroxy-pregn-4-en-3-one-20-carbaldehyde (2.00 g, 5.81 mmol) obtained in the same manner as in Example 1 and the mixture was ice-cooled with stirring. Sodium borohydride (0.11 g, 2.91 mmol) was added to the obtained solution and the mixture was stirred under ice-cooling for 1 hr. 3% Hydrochloric acid was added to the obtained reaction mixture for neutralization, and ethanol was evaporated under reduced pressure. Ethyl acetate (100 ml) and water (20 ml) were added to wash the residue, and the aqueous layer was separated. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give (20S)-7α,21-dihydroxy-20-methyl-pregn-4-en-3-one (1.77 g, yield 88%) having the following property.

Workup

  1. customobtained in the same manner as in Example 1
  2. temperaturecooled
  3. stirringthe mixture was stirred under ice-
  4. temperaturecooling for 1 hr
  5. customwas evaporated under reduced pressure
  6. additionEthyl acetate (100 ml) and water (20 ml) were added
  7. washto wash the residue
  8. customthe aqueous layer was separated
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3a7061671cb84743aad0ccb41c7c2fdb
Source dataset
uspto-grants-2006_12
Patent number
US07153988B2

Reaction notes

Loading…