HuagongsheHuagongshe Chemistry Print Report · For research reference only
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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Piperidinecarboxylic acid | HCID 3773 | — |
| Reactant | 1-(5-Cyano-2-pyridinyl)-4-piperidinecarboxylic acid | HCID 16227474 | — |
| Reactant | rac-[(3R,4S)-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester | HCID 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 ester | HCID 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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09226916B2 |
| Source dataset | uspto-grants-2016_01 |
| ORD ID | ord-28e71123c2e7417997a8873fed0c6bf7 |
| Source note | uspto-grants-2016_01 |