Imidazole → tert-butyl 1-tosyl-2,3-dihydro-1H-benzo[b]azepin-4-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 5-hydroxy-1-tosyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-ylcarbamate (200 mg, 0.46 mmol) and imidazole (94 mg, 1.38 mmol) in toluene (10 mL), triphenylphosphine (242 mg, 262 mmol) and iodine (237 mg, 0.092 mol) were added. The reaction mixture was heated to 110° C. for 3 h. The reaction mixture was cooled to room temperature and diluted with diethyl ether (50 mL). The precipitate that formed was filtered off and the filtrate washed with water followed by a saturated solution of sodium thiosulphate, a saturated solution of sodium bicarbonate and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated under vacuo to give tert-butyl 1-tosyl-2,3-dihydro-1H-benzo[b]azepin-4-ylcarbamate (20 mg, 10.4%).

Provenance & Evidence