Carbon Dioxide → HCID 178483631, compound

Participants

Reaction Conditions

Reaction Steps

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+).

Provenance & Evidence