4-Methylmorpholine → HCID 86742505, compound

Participants

Reaction Conditions

Reaction Steps

0.371 g. (0.001 mole) of (-)-()1S,12bS)-1-ethyl-10-nitro-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-1-yl-propionic acid is added to a solution containing 0.111 g. (0.0011 moles) of N-methylmorpholine (redistilled from sodium) in 4 ml. of dry tetrahydrofuran while stirring under nitrogen, then the solution is cooled to 0° C. and 0.108 g. (0.001 mole) of ethyl chloroformate is rapidly added dropwise while stirring vigorously and keeping the inner temperature at or lower than 0° C. for 30 minutes, whereupon a solution containing 0.133 g. (0.0011 moles) of (R)-1-phenylethylamine in 1 ml. of dry tetrahydrofuran is dropwise added at 0° C. while stirring, finally the mixture is stirred at 0° C. for 30 minutes at room temperature for additional 4 hours. Thereupon the reaction mixture is evaporated on a rotating evaporator and after shaking thoroughly the residue with 10 ml. of dichloromethane and 5 ml. of water, the phases are separated. The dichloromethane solution is washed at first with 5 ml of 5% sodium carbonate solution, then three times with 5 ml of water each, dried over anhydrous magnesium sulphate and evaporated. The crude residue is purified by column chromatography on silica gel by using toluene containing 10% of diethylamine as eluant to give 0.33 g (69.6% yield) of the title compound, M.P.: 130°-132° C., [α]D23 =-140.5 (C=1.0 chloroform) with and Rf value of 0.43 (polygram sil G/UV 254: developed by toluene containing 10% of diethylamine: detected by UV light).

Provenance & Evidence