Hydrochloric Acid → 3-(2-Bromo-3-oxocyclohex-1-enyl)-hexahydro-1-methylazepin-2-one

Participants

Reaction Steps

Lithium diisopropylamide was made from n-butyl lithium (1.55M in hexane, 12.9 ml) and diisopropylamine (2.8 ml) in THF (13 ml). The mixture was treated with 1-methyl-caprolactam (2.54 g) and then with 2-bromo-3-methoxycyclohexenone (4.1 g) in THF (15 ml). After 1 min. the reaction mixture was poured onto 5N HCl (8 ml) and cold water (100 ml). After 0.5 h ether was added and the organic phase separated, dried and evaporated. Recrystallisation of the residue from ethyl acetate gave the title compound (4.9 g), m.p. 112°-115° C. (d). (Found: C, 51.7; H, 6.2; N, 4.7%. C13H18BrNO2 requires: C, 52.0; H, 6.0; 4.7%).

Provenance & Evidence