N-(carbobenzyloxyaminosulfonyl)-2-piperidine-carboxylic acid methyl ester → N-(aminosulfonyl)-2-piperidinecarboxylic acid methyl ester

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Reaction Steps

A solution of N-(carbobenzyloxyaminosulfonyl)-2-piperidinecarboxylic acid methyl ester (29.8 g) in methanol (300 ml) under nitrogen was cooled to 0° C. and 1.8 g of 10% Pd/C was added. The mixture was placed into a Parr Apparatus and hydrogenated for 2 hours at 55 psi. The catalyst was removed on a pad of CELITE® and the filtrate was concentrated in vacuo and purified by flash silica gel chromatography (35-40% ethyl acetate/hexane) to afford 17 g (46%) of N-(aminosulfonyl)-2-piperidinecarboxylic acid methyl ester (Formula VII: R=CH3 ; R1 =H; R2 and R3 together=--(CH2)4 --) as a solid, m.p. 72°-74° C.

Provenance & Evidence