Sodium borohydride → HCID 14320346, compound

HRID 862559Notes

Reaction equation

HRID 862559 reaction equation
[C:1]([O:4][CH:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]2=[O:24])[CH2:6]1)(=[O:3])[CH3:2].[BH4-].[Na+]>CCO.O>[C:1]([O:4][CH:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][CH:14]2[OH:24])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 117593183-Acetoxy-5-androstene-17-one

Product 1

HCID 14320346HCID 14320346, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 100 mg. (0.303 mmol) of 3-acetoxy-androst-5-en-17-one in 3 ml EtOH at -10° C., was added 22.9 mg (0.606 mmol) of sodium borohydride with stirring. After the reaction mixture was stirred for one and 1/2 hours, the mixture was diluted with 10 ml water, the ethanol solvent removed under vacuum, and the residue extracted with ethyl acetate. The organic layer was washed with aqueous Na2CO3, brine, dried over sodium sulfate and concentrated to leave a residue of crude title compound. Proton NMR confirmed the assigned structure.

Workup

  1. stirringAfter the reaction mixture was stirred for one and 1/2 hours
  2. customthe ethanol solvent removed under vacuum
  3. extractionthe residue extracted with ethyl acetate
  4. washThe organic layer was washed with aqueous Na2CO3, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7a2e37a6546c4af58d9b3e4f645da2cd
Source dataset
uspto-grants-1998_02
Patent number
US05719158

Reaction notes

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