HuagongsheHuagongshe Chemistry Print Report · For research reference only
Oxane-4-carboxylic acid → [(3S,4R)-4-(4-chloro-phenyl)-1-(tetrahydro-pyran-4-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Oxane-4-carboxylic acid | HCID 219302 | — |
| Reactant | [(3S,4R)-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester | HCID 67233751 | — |
| Product | [(3S,4R)-4-(4-chloro-phenyl)-1-(tetrahydro-pyran-4-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester | HCID 53244484 | — |
Reaction Steps
In analogy to the procedure described for the synthesis of example 44 (step c), the title compound [(3S,4R)-4-(4-chloro-phenyl)-1-(tetrahydro-pyran-4-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester was prepared from [(3S,4R)-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester instead of rac-[(3S,4R)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester using tetrahydropyran-4-yl-carboxylic acid instead of 1-methylcyclopropane-1-carboxylic acid and was obtained as an off-white foam. MS m/e: 461.2 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09226916B2 |
| Source dataset | uspto-grants-2016_01 |
| ORD ID | ord-232b3089709f43efb1d660abaafbcd68 |
| Source note | uspto-grants-2016_01 |