Bromide ion → tert-Butyl 4-(bromomethylidene)piperidine-1-carboxylate

Participants

Reaction Steps

Lithium bis-trimethylsylylamide (1 M in THF, 7.38 mL, 7.38 mmol) was dropped into a suspension of bromomethyltriphenylphsphonium bromide (3.22 g, 7.38 mmol) at −15° C. under nitrogen atmosphere. After 15 min. under stirring at the same temperature, N-Boc piperidone (1.4 g, 7.03 mmol) dissolved in THF (10 ml) was added. Stirring was maintained and after 2 h at r.t., the reaction mixture was quenched with water and with EtOAc. The combined extracts were washed, dried over Na2SO4 and evaporated to dryness. The crude residue was purified by flash chromatography (EtOAc—Petroleum Ether 98:2) affording the title product (1.27 g).

Provenance & Evidence