Water → 1-tert-Butyl 4-ethyl 5-oxoazepane-1,4-dicarboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 4-oxopiperidine-1-carboxylate (3.2 g, 16 mmol, 1.0 equiv) in Et2O (20 mL) at −50° C. were added BF3.Et2O (2.3 g, 16 mmol, 1.0 equiv) in dropwise. After completion of addition of BF3.Et2O, ethyl 2-diazoacetate (2 g, 17.6 mmol, 1.1 equiv) was added dropwise. The reaction was then stirred at −50° C. for an hour and kept at room temperature overnight. Then the reaction mixture was poured into water (100 mL), extracted with ethyl acetate (3×100 mL), combined of the organic layers and dried over Na2SO4. The solvent was removed under reduced pressure to give the desired product (4 g), which was purified by silica gel chromatography. MS (ESI): 286 (MH+).

Provenance & Evidence