1,1-Dimethylethyl 4-[(4-nitro-2-pyridinyl)oxy]-1-piperidinecarboxylate → HCID 68538138, compound

HRID 1993665Notes

Reaction equation

HRID 1993665 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[C:19]([N+:21]([O-])=O)[CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CCOC(C)=O.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[C:19]([NH2:21])[CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 685380211,1-Dimethylethyl 4-[(4-nitro-2-pyridinyl)oxy]-1-piperidinecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 68538138HCID 68538138, compoundYield 95.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Subject a slurry of 4-(4-nitro-pyridin-2-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (3.0 g, 9.28 mmol) and 5% Pd/C (151 mg) in EtOAc (150 mL) to an atmosphere of hydrogen at 60 psi (Parr shaker) overnight at ambient temperature. Filter the reaction mixture through a pad of Celite® and concentrate under reduced pressure to provide the title compound as a white solid (2.6 g, 95% yield). LCMS ES+(m/z) 294 [M+H].

Workup

  1. customat 60 psi (Parr shaker) overnight
  2. customat ambient temperature
  3. filtrationFilter the reaction mixture through a pad of Celite®
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-b4c289fc824f46bebc438cf6aac865ff
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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