Synthesis of optically active NC-1800, a therapeutic agent for urinary disturbance.

A new synthetic method for chiral oxazolidinone derivatives, therapeutic agents for treating urinary disturbance, is described. The condensed compound obtained from chiral 1-amino-3-phenyl-2-propanol and 1-phenyl-3-morpholino-1-propanone was reduced with Me4NBH(OAc)3 to give the intermediate, 1-(3-morpholino-1-phenylpropyl)amino-3-phenyl-2-propanol (MAPP) in 34% diastereomeric excess (d.e.). MAPP was converted to an urethane and purified by recrystallization of its methanesulfonate, to afford a single isomer, (2R)-1-[N-[(1S)-3-morpholino-1-phenylpropyl]-N -ethoxycarbonyl]amino-3-phenyl-2-propanol methanesulfonate (4-A. methanesulfonate).