Sodium borohydride → HCID 86733133, compound

HRID 267615Notes

Reaction equation

HRID 267615 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([C:22](=[O:24])[CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14](=[CH:15][C:16](=[O:25])[CH2:17][CH2:18]1)[CH2:13][CH2:12]3)=[O:4].[BH4-].[Na+]>CO>[OH:25][C@H:16]1[CH2:17][CH2:18][C@@:19]2([CH3:20])[C:14]([CH2:13][CH2:12][C@@H:11]3[C@@H:21]2[C:22](=[O:24])[CH2:23][C@@:6]2([CH3:7])[C@H:8]3[CH2:9][CH2:10][C@@H:5]2[C:3]([O:2][CH3:1])=[O:4])=[CH:15]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86733134HCID 86733134, compound

Product 1

HCID 86733133HCID 86733133, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

17β-Methoxycarbonylandrost-4-ene-3,11-dione (2.8 g.) was dissolved in dry methanol (250 ml.) and to the stirred solution was added sodium borohydride (600 mg.) in portions over 2 hours. The reaction was then left to stand for 30 minutes, and then concentrated by evaporation under reduced pressure and poured on to ice. The precipitate was extracted into chloroform and the organic solution was dried over sodium sulphate and evaporated to an oil which was purified by preparative TLC to give 3β-hydroxy-17β-methoxycarbonylandrost-4-en-11-one (506 mg.) as colourles plates, m.p. 197°-201°, [α]D 30 144°.

Workup

  1. waitThe reaction was then left
  2. concentrationconcentrated by evaporation under reduced pressure
  3. additionpoured on to ice
  4. extractionThe precipitate was extracted into chloroform
  5. dry with materialthe organic solution was dried over sodium sulphate
  6. customevaporated to an oil which
  7. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-1c7ef05873e048bd9c9b665b8ce326f8
Source dataset
uspto-grants-1976_03
Patent number
US03943124

Reaction notes

Loading…