CONVENIENT SYNTHESIS OF (S)-ALPHA,ALPHA'- DIPHENYL-2-PYRROLIDINEMETHANOL

A convenient synthesis of optically active alpha,alpha'-diphenyl-2-pyr rolidinemethanol(1) starting from L-proline, based on different N-prot ections, was described. Different N-protections had no effect on the o ptical purity of compound 1, but gave different chemical yields. The y ield was the lowest when PhCH2 was employed for N-protection. An inves tigation on the effect of N-protection on the chemical yield and the o ptical purity of compound 1 led to a convenient preparation of the new chiral oxazolidinone 3. The structure of 3 was identified with H-1 NM R, C-13 NMR, MS and IR.