Triethylamine → (2R,4R)-4-Methoxy-2-(4-methoxycarbonyl-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Methyl 4-aminobenzoate	HCID 12082	—
Reactant	2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline	HCID 27833	—
Reactant	(2R,4R)-1-[(tert-butoxy)carbonyl]-4-methoxypyrrolidine-2-carboxylic acid	HCID 11459222	—
Solvent	Chloroform	HCID 6212	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	(2R,4R)-4-Methoxy-2-(4-methoxycarbonyl-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester	HCID 68808041	100.1%

Reaction Steps

Into a solution of 6 (8.11 g, 33.0 mmol) in CHCl3 (200 mL) was added 4-amino-benzoic acid methyl ester (5.00 g, 33.0 mmol), EEDQ (9.81 g, 39.6 mmol), and triethylamine (6.9 mL, 49.6 mmol). The solution was stirred at reflux for 19 h before cooling to RT and adding EtOAc. The solution was washed sequentially with 1N HCl, 0.1N NaOH, water, and brine, before drying over MgSO4 and concentrating under reduced pressure to give 7 (12.50 g, 100%). MS: APCI (AP+): 379.3 (M)+, (AP−): 377.3 (M)−.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07030141B2
Source dataset	uspto-grants-2006_04
ORD ID	ord-4858f61df6ae4da2b152e8fd0cf924c1
Source note	uspto-grants-2006_04