Water → HCID 53939175, compound

HRID 440726Notes

Reaction equation

HRID 440726 reaction equation
[CH:1]([CH2:3][O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[CH:7]([CH2:8][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:2].[BH4-].[Na+].O>CO>[OH:2][CH2:1][CH2:3][O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[CH:7]([CH2:8][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

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86749515HCID 86749515, compound

Product 1

HCID 53939175HCID 53939175, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4.0 g of 3β-formylmethoxy-androstan-17-one in 50 ml of methanol 0.60 g of sodium borohydride were added slowly at -78° C. After 1/2 hr 20 ml of water were added, the methanol was distilled under reduced pressure, and the mixture was extracted with methylene chloride; the organic layer was washed with water, dried over sodium sulfate and evaporated to dryness under reduced pressure. The crude product was purified by flash-chromatography (SiO2) using n-hexane/ethyl acetate 80/20 as eluant to give 3.5 g of the title compound as a white solid.

Workup

  1. distillationthe methanol was distilled under reduced pressure
  2. extractionthe mixture was extracted with methylene chloride
  3. washthe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customThe crude product was purified by flash-chromatography (SiO2)

Sources & evidence

ORD record
ord-9c50a0e0da404e60bc95d9569a3d7289
Source dataset
uspto-grants-1996_05
Patent number
US05521167

Reaction notes

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