Sodium borohydride → HCID 14320346, compound

HRID 2670Notes

Reaction equation

HRID 2670 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-40b377d619b3445095890b35e71e45d2
Source dataset
uspto-grants-1998_03
Patent number
US05730964

Reaction notes

Loading…