Triethylamine → 1-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Participants

Reaction Steps

A solution of methanesulphonyl chloride (20 ml, 0.26 mol) in CH2Cl2 (200 ml) was added dropwise over 15 min to a solution of N-BOC 4-piperidinol (46 g, 0.23 mol) and Et3N (64 ml, 0.46 mol) in CH2Cl2 (430 ml) cooled below 7° C. using a salt/ice bath. After addition was complete, stirring was continued for 15 min. The reaction was warmed to room temperature and quenched with 1N HCl (200 ml). The organic phase was washed with further 1N HCl (200 ml), brine (50 ml), 1N NaOH (100 ml), dried (MgSO4) and evaporated to give 60 g (94% yield) of product as a colourless solid. δH (360 MHz, CDCl3) 1.46 (9H, s), 1.75-1.85 (2H, m), 1.90-2.00 (2H, m), 3.0 (3H, s), 3.25-3.35 (2H, m), 3.65-3.75 (2H, m), 4.85-4.95 (1H, m).

Provenance & Evidence