tert-butyl ((1r,4r)-4-Morpholinocyclohexyl)carbaMate

5414-19-7

177906-48-8

558442-96-9

The general procedure for the synthesis of tert-butyl (trans-4-morpholinocyclohexyl)carbamate from 2,2'-dibromodiethyl ether and tert-butyl trans-(4-aminocyclohexyl)carbamate was as follows: 21.43 g (0.1 mol) of tert-butyl N-(trans-4-aminocyclohexyl)carbamate was dissolved into 250 mL of N,N-dimethylformamide, followed by addition of 16.76 mL (0.12 mol) bis(2-bromoethyl) ether and 34.85 mL (0.25 mol) triethylamine. The reaction mixture was stirred at 70°C for 6 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in ethyl acetate, and the organic layer was washed sequentially with aqueous sodium carbonate and saturated brine solution, and then dried over anhydrous sodium sulfate. The solvent was again removed by reduced pressure distillation and the residue was purified by silica gel column chromatography (elution gradient: from pure chloroform to chloroform/methanol=30/1) to give 19.92 g (70% yield) of tert-butyl (trans-4-morpholino cyclohexyl)carbamate.