Benzyl 2-cyano-3,3-dimethyl-1-pyrrolidinecarboxylate, a versatile intermediate for the synthesis of 3,3-dimethylproline derivatives.

[摘要]：The synthesis of racemic nitrile (?-(I) (Cbz = benzyloxycarbonyl) was accomplished in four steps and 58% overall yield from the known pyrrolidinone. Nitrile (?-I was resolved via preparative chiral HPLC to afford optically pure nitriles (+)-I and (-)-I, from which 3,3-dimethylprolines (+)- and (-)-(II) and (R1 = OH) and 3,3-dimethylprolinamides (+)- and (-)-II (R1 = NH2) could be accessed in nearly quant. yield, without loss of optical purity. The abs. configurations of the resolved prolines and prolinamides were detd. by correlation with an intermediate of known abs. stereochem.

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