1-(1-Methyl-cyclopropanecarbonyl)-piperidine-4-carboxylic acid → HCID 58303141, compound

Participants

Reaction Steps

In analogy to the procedure described for the synthesis of example 44 (step c), the title compounds {(3R,4S)-4-(4-chloro-phenyl)-1-[1-(1-methyl-cyclopropane carbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-methyl-carbamic acid 4,4,4-trifluoro-butyl ester and {(3S,4R)-4-(4-chloro-phenyl)-1-[1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-methyl-carbamic acid 4,4,4-trifluoro-butyl ester were prepared from [(3R,4S)-4-(4-Chloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4,4,4-trifluoro-butyl ester using 1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carboxylic acid instead of 1-methylcyclopropane-1-carboxylic acid and were obtained as a light brown gum. MS m/e: 558.1 [M]+. The racemate was subjected to column chromatography on chiral phase to yield {(3R,4S)-4-(4-chloro-phenyl)-1-[1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-methyl-carbamic acid 4,4,4-trifluoro-butyl ester (MS (m/e): 558.1 [M]+) as an off-white foam and {(3S,4R)-4-(4-chloro-phenyl)-1-[1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-methyl-carbamic acid 4,4,4-trifluoro-butyl ester (MS (m/e): 558.1 [M]+) as an off-white foam.

Provenance & Evidence