Benzyl Bromide → Tert-butyl 5-benzyl-2,4-dioxopiperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 2,4-dioxopiperidine-1-carboxylate (Ark Pharm, Inc., Libertyville, Ill.; 2.0 g, 9.389 mmol) in THF (1 L) at 20° C. was added LHMDS (1.0M in THF; 23.47 mL, 23.47 mmol) (dropwise), and the resulting mixture was stirred at 20° C. for 30 min. Benzyl bromide (3.1 g, 18.77 mmol) was added, and the resulting mixture was stirred at 20° C. for 1 h. The mixture was neutralized with 10M aq. KHSO4 solution and extracted with EtOAc. The organic extract was dried over Na2SO4, filtered, and concentrated in vacuo to provide crude rac-tert-butyl 5-benzyl-2,4-dioxopiperidine-1-carboxylate (1.0 g) (used without further purification in subsequent transformations): m/z (ESI, +ve) 204.0 [(M+H)-100]+.

Provenance & Evidence