Sodium borohydride → (2alpha,3alpha,5alpha,17beta)-2,3-Epoxyandrostan-17-ol

HRID 848788Notes

Reaction equation

HRID 848788 reaction equation
[BH4-].[Na+].[O:3]1[C@H:5]2[CH2:6][C@H:7]3[C@:20]([CH3:22])([CH2:21][C@@H:4]12)[C@@H:19]1[C@H:10]([C@H:11]2[C@@:15]([CH2:17][CH2:18]1)([CH3:16])[C:14](=[O:23])[CH2:13][CH2:12]2)[CH2:9][CH2:8]3>CO>[O:3]1[C@H:5]2[CH2:6][C@H:7]3[C@:20]([CH3:22])([CH2:21][C@@H:4]12)[C@@H:19]1[C@H:10]([C@H:11]2[C@@:15]([CH2:17][CH2:18]1)([CH3:16])[C@@H:14]([OH:23])[CH2:13][CH2:12]2)[CH2:9][CH2:8]3

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13686727HCID 13686727, compound

Product 1

HCID 21139795(2alpha,3alpha,5alpha,17beta)-2,3-Epoxyandrostan-17-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of sodium borohydride (600 mg.) in ice-cold methanol (10 ml.) is added to a solution of 2α,3α-epoxy-5α-androstan-17-one (U.S. Pat. No. 3,169,136, Example I, 1.34 g.) in methanol (60 ml.) and the mixture is stirred at 0° for 30 minutes. The mixture is washed with saline, dried over sodium sulfate and concentrated under reduced pressure to give a residue which is chromatographed on a silica gel column. Appropriate fractions (TLC) are pooled and concentrated to give 2α,3α-epoxy-17β-hydroxy-5α-androstane.

Workup

  1. washThe mixture is washed with saline
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a residue which
  5. customis chromatographed on a silica gel column
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ece536ad0f6244ff8d6701d694909899
Source dataset
uspto-grants-1981_10
Patent number
US04297350

Reaction notes

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