Chlorosuccinimide → ((R)-7-chloro-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl)-carbamic acid tert-butyl Ester

Participants

Reaction Conditions

Reaction Steps

A round-bottom flask containing ((R)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl)-carbamic acid tert-butyl ester (3.09 g, 11.2 mmol) was fitted with a stirbar and septa and flushed with nitrogen. N,N-Dimethylformamide (30 mL) was added, giving a solution that was cooled to 0° C. N-Chlorosuccinimide (2.20 g, 16.5 mmol) was then added, and stirring was continued for 24 hours. The reaction was then poured into ethyl acetate (200 mL) and washed with 1:1 H2O:saturated aqueous NaCl solution (2×100 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo to give a solid that was purified via flash chromatography on silica gel (5% to 30% ethyl acetate/hexanes linear gradient) to give the desired product.

Provenance & Evidence