4-(1-Tert-butoxycarbonyl-piperidin-4-ylmethyl)-3-oxo-piperazine-1-carboxylic acid benzyl ester → 4-(2-Oxo-piperazin-1-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1433086Notes

Reaction equation

HRID 1433086 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]2)[C:13](=[O:31])[CH2:12]1)=O)C1C=CC=CC=1>CO.[Pd]>[C:27]([O:26][C:24]([N:21]1[CH2:22][CH2:23][CH:18]([CH2:17][N:14]2[CH2:15][CH2:16][NH:11][CH2:12][C:13]2=[O:31])[CH2:19][CH2:20]1)=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

4

Reactant 1

HCID 234473564-(1-Tert-butoxycarbonyl-piperidin-4-ylmethyl)-3-oxo-piperazine-1-carboxylic acid benzyl ester

Product 1

HCID 234475144-(2-Oxo-piperazin-1-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-(1-tert-butoxycarbonyl-piperidin-4-ylmethyl)-3-oxo-piperazine-1-carboxylic acid benzyl ester (2.3 g, 5.4 mmol) in methanol (75 mL) is purged with nitrogen and 10% Pd on carbon (0.3 g) is added, and the reaction is again purged with nitrogen. The reaction is placed on a Parr shaker under hydrogen for 16 h. After the system is purged of hydrogen, the catalyst is filtered and washed with methanol. The filtrate is concentrated to provide 4-(2-oxo-piperazin-1-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester which is used without further purification. MS (EI) 298 (M+H)+.

Workup

  1. additionis added
  2. customthe reaction is again purged with nitrogen
  3. customAfter the system is purged of hydrogen
  4. filtrationthe catalyst is filtered
  5. washwashed with methanol
  6. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-da9b6cced0694fb6878e72b9f3d67083
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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