Cycloheptanone → Ethyl 3-methyl-1,4,5,6,7,8-hexahydrocyclohepta[b]pyrrole-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

Ethyl 2,3-dioxobutanoate-2-phenylhydrazone (20.9 g) (T. D; Lash et al., J. Org. Chem. 1992, 57, 4809-4820) in acetic acid (50 ml) was added dropwise to a stirred solution of sodium acetate (10 g), and cycloheptanone (10 g) in acetic acid (100 ml) at 60° C. over 30 minutes. Throughout the addition, small portions of zinc dust (30 g) were added. The reaction was stirred for an additional hour at 80° C., then poured into ice-water (500 g). The resulting solid precipitate was filtered and recrystallised from ethanol to give the product as white needles (2.77 g, 14%), NMR d(CDCl3) 1.38 (3H, t), 1.60-1.95 (6H, m), 2.24 (3H, s), 2.48 (2H, t), 2.68 (2H, t), 4.30 (2H, q), 8.70 (111, bs); M/z (+) 222 (MH+), 176.

Provenance & Evidence