Reaction #554633

ord-ae5f46f7bef043fb87e21b3a77341060

Reaction equation

CC(=O)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]32)C1
5
CC(=O)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]32)C1
3β-Acetoxy-5α-androstan-17-one
[Na+].[OH-]
NaOH
O
water
→
C[C@]12CC[C@H](O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
crude product 6
Yield 95.0%
C[C@]12CC[C@H](O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3β-hydroxy-5α-androstan-17-one
Yield 95.0%

Reactants

CC(=O)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]32)C1
5
CC(=O)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]32)C1
3β-Acetoxy-5α-androstan-17-one
[Na+].[OH-]
NaOH
O
water

Reagents

None

Solvents

CO
methanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturewas refluxed for 10 min
  2. 2
    FiltrationThe resulting precipitate was filtered off
  3. 3
    Washwashed with water

Procedure

A mixture of 5 (1 g, 3.00 mmol), NaOH 0.12 g (3.44 mmol) in methanol was refluxed for 10 min, cooled to room temperature and treated with water. The resulting precipitate was filtered off and washed with water to afford crude product 6 (0.82 g, 95%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08623849B2uspto-grants-2014_01