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

HRID 2396793Notes

Reaction equation

HRID 2396793 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][N:6]1[S:11]([NH:14]C(OCC1C=CC=CC=1)=O)(=[O:13])=[O:12])=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][N:6]1[S:11]([NH2:14])(=[O:13])=[O:12])=[O:4]

Participants

4

Reactant 1

HCID 53700895N-(carbobenzyloxyaminosulfonyl)-2-piperidine-carboxylic acid methyl ester

Product 1

HCID 53861949N-(aminosulfonyl)-2-piperidinecarboxylic acid methyl esterYield 91.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N-(carbobenzyloxyaminosulfonyl)-2-piperidine-carboxylic 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 (90%) 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.

Workup

  1. customThe catalyst was removed on a pad of CELITE®
  2. concentrationthe filtrate was concentrated in vacuo
  3. custompurified by flash silica gel chromatography (35-40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e6e6750ba66c481d957418d1552c37b0
Source dataset
uspto-grants-1996_02
Patent number
US05494925

Reaction notes

Loading…