Sodium Chloride → HCID 20559336, compound

Participants

Reaction Steps

To a stirred solution of 9-ethyl-1,2,3,4-tetrahydro-1,4-ethanocarbazole-2-carboxylic acid (5.0 g, 0.0186 mole, described in Example 3) in dry tetrahydrofuran (50 ml), under nitrogen at 20°-22° C., triethylamine (11.5 ml) was added, followed by ethyl chloroformate (2.8 ml) at 20° C. After stirring at room temperature for 3 hr, the suspension of mixed anhydride was cooled to -10° C. and treated dropwise with a solution of sodium azide (2.94 g in 10 ml of water). The slurries were stirred for 1 hr at -10° C. Water was added and saturated with sodium chloride, then extracted with diethyl ether. The organic layer was washed with water, dried, evaporated to give a yellow oil (ca. 5 g) of 9-ethyl-2,3,4,9-tetrahydro-1,4-ethano-1H-carbazole-2-carbonyl azide: IR (CHCl3) 2135 cm-1.

Provenance & Evidence