Reaction #7507

ord-825838bf0675463188070eeb1a8507bd

Reaction equation

CCCCCCCC(=O)C([NH3+])(C(=O)CCCCCCC)C(=O)CCCCCCC.[Cl-]
Aliquat-336
C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@H]43)[C@@H]1CC[C@@H]2O
19-nortestosterone
→
C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(=O)CC[C@@H]43)[C@@H]1CC[C@@H]2O
title compound
Yield 107.0%
C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(=O)CC[C@@H]43)[C@@H]1CC[C@@H]2O
17β-hydroxy-5β-estran-3-one
Yield 107.0%

Reactants

—
RhCl3.H2O
CCCCCCCC(=O)C([NH3+])(C(=O)CCCCCCC)C(=O)CCCCCCC.[Cl-]
Aliquat-336
C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@H]43)[C@@H]1CC[C@@H]2O
19-nortestosterone

Reagents

None

Solvents

O
water
ClCCl
dichloromethane
ClCCl
dichloromethane

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    WashThe product was washed twice with water (40 ml)
  2. 2
    Otherdried on Na2SO4
  3. 3
    OtherThe catalyst was removed by flash-chromatography on silica gel with CH2Cl2 as eluant

Procedure

A solution of 19-nortestosterone (10.0 g, 35.5 mmol) in dichloromethane (100.0 ml) was mixed with the catalyst previously prepared from RhCl3.H2O (380 mg) and Aliquat-336® (800 mg) in water (10.0 ml) and dichloromethane (22.0 ml). The mixture was hydrogenated overnight at 20 psi. The product was washed twice with water (40 ml) and dried on Na2SO4. The catalyst was removed by flash-chromatography on silica gel with CH2Cl2 as eluant to give 10.5 g (92% yield) the title compound as a white solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07087590B2uspto-grants-2006_08