(R)-3-(2-Nitrophenylamino)piperidine-1-carboxylic acid tertbutyl ester → (R)-3-(2-Aminophenylamino)piperidine-1-carboxylic acid tertbutyl ester

HRID 242819

Reaction equation

HRID 242819 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[NH2:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 59073577(R)-3-(2-Nitrophenylamino)piperidine-1-carboxylic acid tertbutyl ester

Product 1

HCID 59918925(R)-3-(2-Aminophenylamino)piperidine-1-carboxylic acid tertbutyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (R)-3-(2-nitrophenylamino)piperidine-1-carboxylic acid tertbutyl ester (2.48 g, 7.72 mmol) and 10% Pd/C (250 mg) in EtOAc (50 mL) was degassed with a stream of nitrogen and stirred at RT under a hydrogen atmosphere for 20 h. The suspension was then filtered through a PTFE frit and the filtrate was concentrated in vacuo affording (R)-3-(2-Aminophenylamino)piperidine-1-carboxylic acid tertbutyl ester as a clear glass (2.25 g, quantitative). LCMS: RT 2.64 min [M+H-Boc]+ 192.1.

Workup

  1. customwas degassed with a stream of nitrogen
  2. filtrationThe suspension was then filtered through a PTFE frit
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-782192cd7b5c42ae8147566990c677f8
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Linked notes

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