Boron trifluoride etherate → Diethyl 5-oxoazepane-1,4-dicarboxylate

Participants

Reaction Conditions

Reaction Steps

4-Oxo-piperidine-1-carboxylic acid ethyl ester (20 g, 117 mmol) was dissolved in 120 mL Et2O and cooled to −30° C. BF3-OEt2 (14.8 mL) and ethyl diazoacetate (16 mL, 152 mmol) were added simultaneously (each in 15 mL Et2O) over the course of 30 minutes, maintaining an internal temperature of approximately −20° C. The reaction was warmed to room temperature and stirred for 3 hours after which time the reaction was quenched carefully with 30% K2CO3 (60 mL). The organic layer was dried over K2CO3 and concentrated to give 30.4 g of the subtitle compound.

Provenance & Evidence