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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 587384Generated: October 29, 2026

Oxane-4-carboxylic acid → [(3S,4R)-4-(3,4-dichloro-phenyl)-1-(tetrahydro-pyran-4-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-trifluoromethyl-cyclohexyl ester

https://huagongshe.com/reaction/587384

Reaction equation

Participants

RoleNameHCIDCharge
ReactantOxane-4-carboxylic acidHCID 219302—
Reactant[(3S,4R)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-trifluoromethyl-cyclohexyl esterHCID 67234197—
Product[(3S,4R)-4-(3,4-dichloro-phenyl)-1-(tetrahydro-pyran-4-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-trifluoromethyl-cyclohexyl esterHCID 53244541—

Reaction Steps

In analogy to the procedure described for the synthesis of example 44 (step c), the title compound [(3S,4R)-4-(3,4-dichloro-phenyl)-1-(tetrahydro-pyran-4-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-trifluoromethyl-cyclohexyl ester was prepared from [(3S,4R)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-trifluoromethyl-cyclohexyl ester instead of [(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: 551.4 [M]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09226916B2
Source datasetuspto-grants-2016_01
ORD IDord-0e639710f4cf46d1bfdf5e9ad587cc84
Source noteuspto-grants-2016_01