Triethylamine → Benzyl 5,6-dihydropyridine-1(2H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of 1,2,3,6-tetrahydropyridine (5.0 g) in dichloromethane (200 mL) was cooled to 0° C. and treated with triethylamine (10.1 mL) followed by benzylchloroformate (10.3 mL). The reaction mixture was stirred for 1 hour at 0° C., diluted with dichloromethane, washed (dilute hydrochloric acid, sodium bicarbonate solution), dried and evaporated. The crude product was distilled to give the N-protected derivative (11.01 g); bp 160°-165° C. (26.7 Pa); NMR (CDCl3): 2.15 (broad, 2), 3.5 (t,2, J=6), 3.96 (m, 2), 5.15 (s, 2), 5.8 (2 broad peaks, 2), 7.4(m, 5); MS: m/z=218(M+1).

Provenance & Evidence