Carbon tetrabromide → 183170-70-9

Participants

Reaction Steps

In dichloromethane (20 ml) was dissolved N-tert-butoxycarbonyl-4-(1-hydroxyethyl)piperidine (0.92 g). After addition of carbon tetrabromide, (1.62 g), triphenylphosphine (1.58 g) was slowly added under ice-cooling. The mixture was stirred at room temperature for 2 hours, at the end of which time the dichloromethane was distilled off. The residue was diluted with ethyl acetate and an aqueous solution of NaHCO3 and the insoluble matter was filtered off. The filtrate was extracted with ethyl acetate, washed with aqueous NaCl solution, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography (hexane: ethyl acetate =8:1) to provide the title compound as colorless oil (1.34 g). 1H-NMR (CDCl3) δ: 1.0-1.3(3H,m), 1.4;5(9H,s), 1.6-1.9(4H,m), 2.6-2.8(2H,brm), 3.45(2H,t,J=6.8Hz), 4.0-4.2(2H,brm).

Provenance & Evidence