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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 79929Generated: October 29, 2026

Triethylamine → 4,4-Difluoro-pyrrolidine-1,2-dicarboxylic acid 2-[2-(6-bromo-naphthalen-2-yl)-2-oxo-ethyl]ester 1-tert-butyl ester

https://huagongshe.com/reaction/79929

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactant2-Bromo-1-(6-bromonaphthalen-2-yl)ethanoneHCID 12698898—
Reactant1-((Tert-butoxy)carbonyl)-4,4-difluoropyrrolidine-2-carboxylic acidHCID 23512514—
SolventAcetonitrileHCID 6342—
Product4,4-Difluoro-pyrrolidine-1,2-dicarboxylic acid 2-[2-(6-bromo-naphthalen-2-yl)-2-oxo-ethyl]ester 1-tert-butyl esterHCID 6662086483%

Reaction Steps

2-Bromo-1-(6-bromo-naphthalen-2-yl)-ethanone (1 g, 3.07 mmol) and 4,4-Difluoro-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (849 mg, 3.38 mmol) were suspended in MeCN (15 mL) and treated with Et3N (0.45 mL, 3.22 mmol). After stirring o/n, the reaction mixture was concentrated. The resulting residue was dissolved in EtOAc and washed with water, saturated aqueous NaHCO3 and brine. The organic layer was dried over MgSO4, filtered and concentrated. The crude material was purified by silica column chromatography (0% to 20% EtOAc/Hex) to provide the title compound (1.27 g, 83%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08841278B2
Source datasetuspto-grants-2014_09
ORD IDord-47dc7af68cd54249a8c1be009e2f617e
Source noteuspto-grants-2014_09