Methanesulfonyl chloride → Benzyl 4-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate

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A solution of methanesulphonylchloride (7.7 ml) in dichloromethane (50 ml) was added dropwise to a stirred solution of 1-benzyloxycarbonyl-4-hydroxymethylpiperidine (23.4 g) in dichloromethane (350 ml) cooled to 5° C. Stirring was continued for 1 hour, then the solution was washed with water (4×150 ml) and saturated aqueous sodium chloride (100 ml), dried and concentrated. The residue was crystallised from tetrachloromethane (250 ml) to give 1-benzyloxycarbonyl-4-methanesulphonyloxymethylpiperidine (20 g) as colourless prisms, m.p. 72°-74° C. NMR (CDCl3) δ1.1-1.4(2H,m); 1.7-1.8(2H,d); 1.9-2.1(1H,m); 2.7-2.9(2H,t); 3.0(3H,s); 4.05(2H,d); 4.1-4.4(2H,d); 5.1(2H,s); 7.3(5H,m); m/e 328(M+H)+350 (M+Na)+ ; calculated for C15H21N5 O5 : C, 55.0;H, 6.5; N, 4.3; found: C, 54.8; H, 6.6; N, 4.2%.

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