Methyl1-Boc-4-[[(R)-1-phenylethyl]amino]piperidine-3-carboxylate → 1-O-tert-butyl 3-O-methyl 4-aminopiperidine-1,3-dicarboxylate

HRID 736750Notes

Reaction equation

HRID 736750 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH:10]([NH:11]C(C2C=CC=CC=2)C)[CH2:9][CH2:8][N:7]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:6]1)=[O:4]>CO.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3]([CH:5]1[CH:10]([NH2:11])[CH2:9][CH2:8][N:7]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:6]1)=[O:4]

Participants

4

Reactant 1

HCID 68819527Methyl1-Boc-4-[[(R)-1-phenylethyl]amino]piperidine-3-carboxylate

Product 1

HCID 592166281-O-tert-butyl 3-O-methyl 4-aminopiperidine-1,3-dicarboxylateYield 81.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(1-phenyl-ethylamino)-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (2.4 g, 6.62 mmol) and 20% palladium hydroxide on carbon (1 g) in methanol (20 mL) was stirred under a hydrogen balloon for 19 h. The mixture was then filtered through a thin pad of celite and concentrated to provide 4-amino-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester as a colorless oil (1.3 g, 81.2%) MS: 259 (M+H)+.

Workup

  1. filtrationThe mixture was then filtered through a thin pad of celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-f1ede11580de4abc8325c22ce8265d9b
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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