反应详情

6-[(E)-3-tert-Butyldimethylsilyloxy-3-cyclohexylprop-1-enyl]-3-[(E)-4-methoxycarbonylbutylidene]bicyclo[3,3,0]octane-2-one (12 mg), prepared as described in Reference Example 15 and in the form of (±)-6β-[(E)-3β-tert-butyldimethylsilyloxy-3-cyclohexylprop-1-enyl]-3-[(E)-4-methoxycarbonylbutylidene]bicyclo[3,3,0]octan-2-one, otherwise known as (±)-methyl(5E,13E)-(9S,15S)-6a-oxo-6,9-methano-15-tert-butyldimethylsilyloxy-15-cyclohexyl-16,17,18,19,20-pentanorprosta-5,13-dienoate, and a solution of water, glacial acetic acid and tetrahydrofuran (0.5 ml; 35:65:10 by volume) were stirred together at 40° C. for 4 hours. After cooling, the mixture was diluted with saturated aqueous sodium chloride solution and extracted with diethyl ether. The ethereal extracts were washed with aqueous sodium bicarbonate solution (1M) and then with saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulphate. Concentration under reduced pressure gave 6-[(E)-3-cyclohexyl-3-hydroxyprop-1-enyl]-3-[(E)-4-methoxycarbonylbutylidene]bicyclo[3,3,0]octan-2-one (12.7 mg), in the form of (35)-6β-[(E)-3-cyclohexyl-3β-hydroxyprop-1-enyl]-3-[(E)-4-methoxycarbonylbutylidene]bicyclo[3,3,0]octan-2-one, otherwise known as (±)-methyl(5E,13E)-(9S,15S)-6a-oxo-6,9-methano-15-cyclohexyl-15-hydroxy-16,17,18,19,20-pentanorprosta-5,13-dienoate.

1. temperatureAfter cooling
2. extractionextracted with diethyl ether
3. washThe ethereal extracts were washed with aqueous sodium bicarbonate solution (1M)
4. dry with materialwith saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulphate
5. concentrationConcentration under reduced pressure