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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 587364Generated: October 30, 2026

4-Piperidinecarboxylic acid → [(3S,4R)-4-(4-Chloro-phenyl)-1-(5'-cyano-3,4,5,6-tetrahydro-2H-[1,2]bipyridinyl-4-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester

https://huagongshe.com/reaction/587364

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-Piperidinecarboxylic acidHCID 3773—
Reactant1-(5-Cyano-2-pyridinyl)-4-piperidinecarboxylic acidHCID 16227474—
Reactantrac-[(3R,4S)-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl esterHCID 67234029—
Product[(3S,4R)-4-(4-Chloro-phenyl)-1-(5'-cyano-3,4,5,6-tetrahydro-2H-[1,2]bipyridinyl-4-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl esterHCID 58303011—

Reaction Steps

In analogy to the procedure described for the synthesis of example 1 (step f), the title compound rac-[(3S,4R)-4-(4-Chloro-phenyl)-1-(5′-cyano-3,4,5,6-tetrahydro-2H-[1,2]bipyridinyl-4-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester was prepared from rac-[(3R,4S)-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester instead of rac-[(3R,4S)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester using 5′-cyano-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid instead of 141-methyl-cyclopropanecarbonyl)-piperidine-4-carboxylic acid and was obtained as an orange oil. MS m/e: 524.3 [M]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09226916B2
Source datasetuspto-grants-2016_01
ORD IDord-28e71123c2e7417997a8873fed0c6bf7
Source noteuspto-grants-2016_01