tert-butyl N-[(1S,3R)-3-(hydroxymethyl)cyclohexyl]carbamate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of tert-butyl[cis-3-(hydroxymethyl)cyclohexyl]carbamate (311 mg) in EtOAc (3.1 ml) was added 4M HCl in EtOAc which was stirred at ambient temperature for 1 hour. Resulting precipitates were collected by filtration and washed with diisopropyl ether to give [cis-3-aminocyclohexyl]methanol hydrochloride (236 mg) as a white powder. Resulting precipitates were collected by filtration washed with diisopropyl ether

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of cis-3-[(tert-butoxycarbonyl)amino]-cyclohexanecarboxylic acid (500 mg) in tetrahydrofuran (5 ml) was added triethylamine (344 μl) and isobutyl chloroformate (320 μl) under stirring at 0° C. After stirring at 0° C. for 1 hour, sodium borohydride (233 mg) was added, and methanol (5 ml) was added dropwise under stirring at 0° C. After stirring at 0° C. for 1 hour, 10% aqueous potassium hydrogen sulfate (10 ml) was added and neutralized with saturated aqueous sodium hydrogencarbonate. and extracted with EtOAc. The organic layer was washed with water, brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by preparative thin layer chromatography on silica gel eluting with n-hexane:EtOAc=70:30 to 40:60 to give tert-butyl[cis-3-(hydroxymethyl)cyclohexyl]carbamate (311 mg) as a white powder. After stirring at 0° C. for 1 hour under stirring at 0° C After stirring at 0° C. for 1 hour and extracted with EtOAc The organic layer was washed with water, brine dried over MgSO4 concentrated in vacuo The residue was purified by preparative thin layer chromatography on silica gel eluting with n-hexane