N-(chloromethyloxycarbonyl)pyrrolidine as a source of the HOCH2- synthon

Article abstract of DOI:10.1016/0040-4039(96)01133-1

The reaction of N-(chloromethyloxycarbonyl)pyrrolidine (1) with lithium powder and a catalytic amount of DTBB (2.5 mol %) in the presence of different electrophiles [Me₃SiCl, Bu(i)CHO, Bu(t)CHO, PhCHO, Et₂CO, (CH₂)₅CO, PhCOMe, Ph₂CO] in THF at -78°C leads, after hydrolysis with water, to the expected functionalised carbamates 2. Deprotection of the acetophenone derivative 2g with DIBALH at THF reflux yields, after hydrolysis, the corresponding 1,2-diol 3g.