Methyl [1-(5-nitropyridin-2-yl)piperidin-4-yl]acetate → Methyl [1-(5-aminopyridin-2-yl)piperidine-4-yl]acetate

HRID 557691Notes

Reaction equation

HRID 557691 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][N:12]=2)[CH2:7][CH2:6]1>O1CCCC1.CO.[Pd]>[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH:5]1[CH2:6][CH2:7][N:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][N:12]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 1

HCID 47357980Methyl [1-(5-nitropyridin-2-yl)piperidin-4-yl]acetate

Product 1

HCID 59464078Methyl [1-(5-aminopyridin-2-yl)piperidine-4-yl]acetate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-acetic acid methyl ester (279 mg, 1 mmol) from above in a mixture of tetrahydrofuran (10 mL) and methanol (50 mL) was added 10% palladium on carbon (50 mg). The mixture was hydrogenated at 50 psi for 1 hr. The mixture was filtered and the solvents were evaporated to give (5′-amino-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-acetic acid methyl ester that was used in the next step without further purification.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvents were evaporated

Sources & evidence

ORD record
ord-1f5b0e17aef848de8c3095c194e7ae5a
Source dataset
uspto-grants-2011_11
Patent number
US08058299B2

Reaction notes

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