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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 490629Generated: October 25, 2026

Acetic Acid → Benzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidine-2-carboxylic acid methyl ester

https://huagongshe.com/reaction/490629

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
Reactant3,5-Bis(trifluoromethyl)benzylamineHCID 521099—
ReactantSodium triacetoxyborohydrideHCID 5049666—
ReactantBenzyl-4-oxo-pyrrolidine-2-carboxylic acid methyl esterHCID 67548133—
SolventDichloromethaneHCID 6344—
ProductBenzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidine-2-carboxylic acid methyl esterHCID 8662530063%

Reaction Steps

Benzyl-4-oxo-pyrrolidine-2-carboxylic acid methyl ester (100 mg, 0.428 mmol) and 3,5-bis-trifluoromethyl-benzylamine (125 mg, 0.514 mmol) were dissolved in dry DCM (2 mL), acetic acid (0.1 mL) and NaBH(OAc)3 (180.6 mg, 0.856 mmol) was then added. After stirred for 3 hours the reaction mixture was diluted with DCM, washed with saturated NaHCO3 (cautiously), dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography to afford the title product 1-benzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidine-2-carboxylic acid methyl ester 124 mg (63%) as a yellow oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07528136B2
Source datasetuspto-grants-2009_05
ORD IDord-c07eb75d69254aa99897fdb1cf0a859d
Source noteuspto-grants-2009_05