Ethanol → HCID 15679290, compound

Participants

Reaction Steps

(R)-Prolinamide hydrochloride was prepared according to G. Flouret et al. J. Med.Chem. 16 (1973) 1137 in a yield of 64% (lit. 53%); mp 180°-181° C. (lit 178°-180° C.); [α]D22 +67° (c=0.80, EtOH) (lit. [α]D23 =+69.5° (c=2, EtOH). To a mixture of (R)-prolinamide hydrochloride (4.3 g, 23 mmol) and K2CO3 (8.3 g, 60 mmol) in 20 ml dry DMSO was added a solution of p-fluorobenzylbromide (4.5 g, 23.5 mmol) in 3 ml DMSO at room temperature. The reaction mixture was stirred overnight, poured into 200 ml of ice-water and extracted twice with ET2O. The organic layer was washed with water, dried (Na2SO4) and evaporated. The residue was recrystallized from iPr2O to give 3.0 g (59%) pure title compound, mp 82°-83° C.; [α]D22 =+77° (c=0.8, CHCl3) From the mother liquor was obtained another 1.0 g (20%).

Provenance & Evidence