N,N,N',N',N'',N''-Hexamethylmethanetriamine → 5-Dimethylaminomethylene-4-oxo-1,4,5,6,7,8-hexahydro-cyclohepta[b]pyrrole-3-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]pyrrole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (1.13 g, 3.52 mmol) and tris(dimethylamino)methane (1.02 g, 7.04 mmol) is stirred at 60° C. in a sealed tube for 4.5 h. After cooling, the thick slurry is taken up in Et2O and filtered. The solid is washed with Et2O and dried, affording 847 mg (87%) of 5-dimethylaminomethylene-4-oxo-1,4,5,6,7,8-hexahydro-cyclohepta[b]pyrrole-3-carboxylic acid ethyl ester as a light yellow-orange solid. 1H NMR (CDCl3, 300 MHz) δ9.93 (br s, 1H), 7.58 (s, 1H), 7.12 (d, J=2.7 Hz, 1H), 4.21 (q, J=7.2 Hz, 2H), 3.06 (s, 6H), 2.68 (m, 2H), 2.47 (m, 2H), 1.80 (m, 2H), 1.26 (t, J=7.2 Hz, 3H).

Provenance & Evidence