Triethylamine → 3-Furancarboxamide,tetrahydro-N-methoxy-N-methyl-(9CI)

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Methanamine, N-methoxy-, hydrochloride (1:1)	HCID 81138	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	(R)-Tetrahydro-3-furoic acid	HCID 4661317	—
Solvent	Dichloromethane	HCID 6344	—
Product	3-Furancarboxamide,tetrahydro-N-methoxy-N-methyl-(9CI)	HCID 45084522	49%

Reaction Steps

Into a 250-mL round-bottom flask, was placed a solution of tetrahydrofuran-3-carboxylic acid (10 g, 86.1 mmol) in dichloromethane (200 mL). EDC.HCl (18.2 g, 94.9 mmol), N,O-dimethylhydroxylamine hydrochloride (10 g, 103 mmol) and triethylamine (24.0 mL, 172 mmol) were added and the resulting mixture was stirred overnight at room temperature. The mixture was diluted with DCM (50 mL) and washed with aqueous HCl (1 M, 3×10 mL), sodium bicarbonate (sat., 2×30 mL) and brine (3×20 mL). The organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure to obtain the title compound as light yellow oil (6.71 g, 49%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09428502B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-43b450cd30b749d4bdf4cf800a28c1fa
Source note	uspto-grants-2016_08