Abstract We document an efficient and cost??effective synthesis of ramipril 1 utilizing (i) an environmentally benign process for the esterification of racemic 2??aza??bicyclo??[3.3. 0]?? octane??3??carboxylic acid hydrochloride 2 using boric acid as a catalyst and (ii) a robust resolution process for the synthesis of 3a by means of inexpensive and recyclable L??(+)?? mandelic acid as key steps.