Nicotinic Acid → 1-(Pyridine-3-carbonyl)-pyrrolidine-2-carboxylic acid methyl ester

Participants

Role	Name	HCID	Charge
Reactant	Nicotinic Acid	HCID 938	—
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	Methyl L-prolinate	HCID 853477	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Dichloromethane	HCID 6344	—
Product	1-(Pyridine-3-carbonyl)-pyrrolidine-2-carboxylic acid methyl ester	HCID 43409998	172.9%

Reaction Conditions

Temperature	25 °C

Reaction Steps

To a solution of niacin (0.4 g 3.50 mmol) in DCM (10 mL) were added L-proline methyl ester (0.5 g, 3.21 mmol), N-methyl morpholine (1.1 mL, 0.10.5 mmol), EDC.HCl (1.2 g, 6.4 mmol) and catalytic amount of DMAP at ice temperature (0° C.). The mixture was allowed to stir at room temperature (25° C.) over a period of 2 h. The resulting mixture diluted with DCM (100 mL) washed with water (2×100 mL) and dried over sodium sulphate. Solvent was evaporated under reduced pressure to obtain product as yellow gummy oil (1.3 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08846721B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-3733038fe77a4ef3b693f11951fb0d39
Source note	uspto-grants-2014_09