Triethylamine → 3,3a,4,5,6,6a-hexahydro-2H-pentalen-1-one

Participants

Reaction Steps

A stirred solution of 6-[(E)-3-tert-butyldimethylsilyloxy-3-cyclohexylprop-1-enyl]-3-(5-ethoxycarbonyl-2-hydroxypent-2-yl)bicyclo[3,3,0]octan-2-one (26 mg), prepared as described in Reference Example 39 and in the form of 6β-[(E)-3β-tert-butyldimethylsilyloxy-3-cyclohexylprop-1-enyl]-3-(5-ethoxycarbonyl-2-hydroxypent-2-yl)bicyclo[3,3,0]octan-2-one, otherwise known as (±)-ethyl(13E)-(9S,15R)-6a-oxo-6,9-methano-15-tert-butyldimethylsilyloxy-15-cyclohexyl-5-hydroxy-5-methyl-16,17,18,19,20-pentanorprost-13-enoate, in benzene (0.19 ml) was treated with methanesulphonyl chloride (0.0048 ml) at the ambient temperature, followed by triethylamine (0.008 ml) and the mixture was stirred for 2 hours. It was then treated with 1,8-diazabicyclo[5,4,0]undec-7-ene (0.0446 ml) and the mixture was stirred for 2 hours. It was then treated with water (10 ml) and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulphate, and concentrated under reduced pressure. The resulting residue was subjected to medium pressure, short column chromatography on silica gel, using a mixture of ethyl acetate and hexane (1:8 v/v) as eluant, to give 6-[(E)-3-tert-butyldimethylsilyloxy-3-cyclohexylprop-1-enyl]-3-{[mixture of (E) and (Z)]-5-ethoxycarbonylpentylid-2-ene}bicyclo[3,3,0]octan-2-one (22 mg), in the form of (±)-6β-[(E)-3β-tert-butyldimethylsilyloxy-3-cyclohexylprop-1-enyl]-3-{[mixture of (E) and (Z)]-5-ethoxycarbonylpentylid-2-ene}bicyclo[3,3,0]octan-2-one, otherwise known as (±)-ethyl [mixture of (5E and (5Z)],(13E)-(9S,15R)-6a-oxo-6,9-methano-5-methyl-15-tert-butyldimethylsilyloxy-15-cyclohexyl-16,17,18,19,20-pentanorprosta-5,13-dienoate.

Provenance & Evidence