1-Methanesulfonyl-piperidine-4-carboxylic acid benzyl ester → 1-Methanesulfonylpiperidine-4-carboxylic acid

HRID 2103990Notes

Reaction equation

HRID 2103990 reaction equation
C([O:8][C:9]([CH:11]1[CH2:16][CH2:15][N:14]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][CH2:12]1)=[O:10])C1C=CC=CC=1>C(OCC)(=O)C.CO.[Pd]>[CH3:20][S:17]([N:14]1[CH2:15][CH2:16][CH:11]([C:9]([OH:10])=[O:8])[CH2:12][CH2:13]1)(=[O:19])=[O:18]

Participants

5

Reactant 1

HCID 574280631-Methanesulfonyl-piperidine-4-carboxylic acid benzyl ester

Product 1

HCID 7740121-Methanesulfonylpiperidine-4-carboxylic acidYield 73%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Methanesulfonyl-piperidine-4-carboxylic acid benzyl ester (0.8 g, 26.7 mmol) from step 4, was dissolved in ethyl acetate (100 ml) and methanol (10 ml), Pd/C 10% (80 mg) was added and the resulting mixture was hydrogenated at 1 bar. The catalyst was filtered over celite, the solvent was removed under reduced pressure to give a white solid. Yield 73%, 0.4 g.

Workup

  1. filtrationThe catalyst was filtered over celite
  2. customthe solvent was removed under reduced pressure
  3. customto give a white solid

Sources & evidence

ORD record
ord-40207913a347496ca30f89712720b67c
Source dataset
uspto-grants-2009_08
Patent number
US07576206B2

Reaction notes

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