反应详情

温度

-75 °C

To a dry ice-cooled solution of 4 g (11.8 mmol) trans-3-{4-[2-(tert-butoxycarbonyl-methyl-amino)-ethyl]-cyclohexyl}-(E)-acrylic acid ethyl ester (example 11.10) in 50 ml of tetrahydrofuran was added at −75° C. to −63° C. within 15 minutes 23.6 ml (28.3 mmol) of a solution of diisobutyl-aluminium hydride (1.2M in toluene). After the reaction mixture was stirred for 2 hours at −75° C., 20 ml of methanol was added at −75° C. to this mixture. The temperature was raised to 20° C. and 20 ml 1N hydrogen chloride solution was added. The reaction mixture was partitioned between ether, 1N hydrogen chloride solution, sodium hydrogen carbonate solution and water. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure giving 3.61 g of trans-{2-[4-(3-hydroxy-(E)-propenyl)-cyclohexyl]-ethyl}-methyl-carbamic acid tert-butyl ester as slightly yellow viscous oil, MS: 298 (MH+).

1. temperatureThe temperature was raised to 20° C.
2. customThe reaction mixture was partitioned between ether, 1N hydrogen chloride solution, sodium hydrogen carbonate solution and water
3. dry with materialThe organic layer was dried over magnesium sulfate
4. concentrationconcentrated under reduced pressure