Triethylamine → 2-Phenyl-cyclopropanecarboxylic acid(2-hydroxy-1-naphthalen-2-yl-ethyl)-amide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	2-Phenylcyclopropane-1-carboxylic acid	HCID 70323	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	(R)-2-Amino-2-(naphthalen-2-yl)ethanol	HCID 8027555	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Dichloromethane	HCID 6344	—
Product	2-Phenyl-cyclopropanecarboxylic acid(2-hydroxy-1-naphthalen-2-yl-ethyl)-amide	HCID 21864682	78.5%

Reaction Steps

A mixture of (R)-2-amino-2-naphthalen-2-yl-ethanol (0.2 mmol), 2-phenyl-cyclopropanecarboxylic acid (0.2 mmol), EDAC.HCl (0.4 mmol), DMAP (0.2 mmol), and triethylamine (0.6 mmol) in dichloromethane (2 mL) was stirred at room temperature for 12 h. The reaction mixture was purified by flash chromatography eluting with 50% hexanes in ethyl acetate to give the desired product (52 mg) as a solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07144881B2
Source dataset	uspto-grants-2006_12
ORD ID	ord-a309c780d9f24f10a68d218b32a3221f
Source note	uspto-grants-2006_12