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

HRID 743474Notes

Reaction equation

HRID 743474 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 94.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N-(carbobenzyloxyaminosulfonyl)-2-piperidinecarboxylic acid methyl ester (28.8 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®and the filtrate
  2. concentrationwas concentrated in vacuo
  3. custompurified by flash silica gel chromatography (35%-40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7d08b581e57940f688458dc82abec37d
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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