HCID 45786893, compound → 1,1-Dimethylethyl 4-[(5-amino-2-pyridinyl)oxy]-1-piperidinecarboxylate

HRID 1993659Notes

Reaction equation

HRID 1993659 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)=[CH:17][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])=[CH:17][N:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 45786893HCID 45786893, compound

Product 1

HCID 510636931,1-Dimethylethyl 4-[(5-amino-2-pyridinyl)oxy]-1-piperidinecarboxylateYield 86.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Stir a mixture of 4-(5-Nitro-pyridin-2-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (2.7 g, 8.35 mmol) and 10% palladium on carbon (0.5 g) in ethanol (100 mL) at room temperature under hydrogen for 4 hours. Filter to remove palladium catalyst. Concentrate the filtrate and subject the resultant colorless oil to silica gel chromatography eluting with hexanes and ethyl acetate to give the title compound as a white solid (2.11 g, 86% (ES+(m/z) 194.2 [M+H—BOC]).

Workup

  1. filtrationFilter
  2. customto remove palladium catalyst
  3. concentrationConcentrate the filtrate
  4. washeluting with hexanes and ethyl acetate

Sources & evidence

ORD record
ord-b3375842a73543e2af7791ea845e64f3
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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