Methyl morpholine oxide → 14beta,15beta-Epoxy-17beta-(3-furyl)-5beta-androstan-3-one

HRID 1647640Notes

Reaction equation

HRID 1647640 reaction equation
[O:1]1[C@@H:3]2[CH2:4][C@H:5]([C:22]3[CH:26]=[CH:25][O:24][CH:23]=3)[C@:6]3([CH2:8][CH2:9][C@H:10]4[C@H:19]([C@@:2]123)[CH2:18][CH2:17][C@H:16]1[C@:11]4([CH3:21])[CH2:12][CH2:13][C@H:14]([OH:20])[CH2:15]1)[CH3:7].C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[O:1]1[C@@H:3]2[CH2:4][C@H:5]([C:22]3[CH:26]=[CH:25][O:24][CH:23]=3)[C@:6]3([CH2:8][CH2:9][C@H:10]4[C@H:19]([C@@:2]123)[CH2:18][CH2:17][C@H:16]1[C@:11]4([CH3:21])[CH2:12][CH2:13][C:14](=[O:20])[CH2:15]1)[CH3:7]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 8674878814beta,15beta-Epoxy-17beta(3-furyl)-5beta-androstan-3beta-ol

Product 1

HCID 8674878714beta,15beta-Epoxy-17beta-(3-furyl)-5beta-androstan-3-oneYield 158.9%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.0 g of 14β,15β-epoxy-17β-(3-furyl)-5β-androstan-3β-ol (E. Yoshii et al., Chem. Pharm. Bull., 1976, 24, 3216) in 70 ml of methylene chloride, 2.5 g of 4-methylmorpholine N-oxide, 0.25 g of tetrapropylammonium perruthenate and 4.0 g of powdered 4A molecular sieves were added at room temperature. After 4 hrs the solvent was evaporated to dryness under reduced pressure and the crude product purified by flash-chromatography (SiO2) using n-hexane/ethyl acetate 70/30 as eluant to give 7.9 g of 14β,15β-epoxy-17β-(3-furyl)-5β-androstan-3-one as a white solid.

Workup

  1. customAfter 4 hrs the solvent was evaporated to dryness under reduced pressure
  2. customthe crude product purified by flash-chromatography (SiO2)

Sources & evidence

ORD record
ord-5433a7293a82450387910f2a16ff036f
Source dataset
uspto-grants-1995_07
Patent number
US05432169

Reaction notes

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