Sodium borohydride → HCID 14320346, compound

HRID 726862Notes

Reaction equation

HRID 726862 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, 1, 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 2. 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-77d735f4a76f49a4b54d360fc4905921
Source dataset
uspto-grants-1998_01
Patent number
US05710275

Reaction notes

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