Diethyl Ether → (R)-1-(2-bromoethyl)nipecotic acid ethyl ester hydrobromide

Participants

Reaction Steps

A sample of the above alcohol (140 g, 0.70 mole) was dissolved in toluene (400 ml) and thionyl bromide (80 ml, 0.77 mole) was introduced with vigorous stirring. After 1.5 h the exotherm reaction had subsided and diethyl ether (400 ml) was added. The resultant precipitate was collected by filtration and washed with diethyl ether. The solid was triturated with ethyl acetate, again collected on a filter and dried to provide (R)-1-(2-bromoethyl)nipecotic acid ethyl ester hydrobromide (175 g, 73%) as a white solid, m.p. 210°-215° C.

Provenance & Evidence