4-(6-Methyl-5-nitro-pyridin-2-yloxy)-piperidine-1-carboxylic acid tert-butyl ester → 4-(5-Amino-6-methyl-pyridin-2-yloxy)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1993657Notes

Reaction equation

HRID 1993657 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[C:17]([CH3:24])[N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[C:17]([CH3:24])[N:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 685353024-(6-Methyl-5-nitro-pyridin-2-yloxy)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 591344504-(5-Amino-6-methyl-pyridin-2-yloxy)-piperidine-1-carboxylic acid tert-butyl esterYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Stir a mixture of 4-(6-methyl-5-nitro-pyridin-2-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (2.69 g, 8.0 mmol) and 10% palladium on carbon (1.0 g) in ethanol (60 mL) at 22° C. under hydrogen for 2 hours. Filter off the palladium catalyst. Concentrate the filtrate to give a colorless oil. Subject residue to silica gel chromatography eluting with hexanes and ethyl acetate to give the title compound. (2.19 g, 89% yield). MS(ES): m/z=308.2 [M+H].

Workup

  1. filtrationFilter off the palladium catalyst
  2. concentrationConcentrate the filtrate
  3. customto give a colorless oil
  4. washSubject residue to silica gel chromatography eluting with hexanes and ethyl acetate

Sources & evidence

ORD record
ord-f65493e9af1a434683fedd7ca7d32ef4
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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