AN EFFICIENT SYNTHESIS OF (R)-(+)- AND (S)-(-)-PROPRANOLOL FROM RESOLVED 5-IODOMETHYLOXAZOLIDIN-2-ONES

Article abstract of DOI:10.1016/S0040-4020(01)81657-4

(1'S^*,5S,R)-3-(1'-phenyleth-1'-yl)-5-iodomethyloxazolidin-2-ones, 4a,b, have been synthesized and easily resolved by silica gel chromatography.Each pure diastereomer has been then converted to (S)-(-)-propranolol 1a and (R)-(+)-propranolol 1b, respectively.An empirical correlation of configuration and ¹H NMR chemical shift for alternate diastereomers has been devised and has proved to be applicable in assigning the configuration of 5-substituted 3-(1'-phenyleth-1'-yl)oxazolidin-2-ones.