4-(3-Methyl-5-nitropyridin-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylic acid tert-butyl ester → 4-(5-Amino-3-methylpyridin-2-yl)piperidine-1-carboxylic acid tert-butyl ester

HRID 1748589Notes

Reaction equation

HRID 1748589 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:19]([CH3:20])=[CH:18][C:17]([N+:21]([O-])=O)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[C].[Pd].O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[C:19]([CH3:20])=[CH:18][C:17]([NH2:21])=[CH:16][N:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 866925414-(3-Methyl-5-nitropyridin-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 866925404-(5-Amino-3-methylpyridin-2-yl)piperidine-1-carboxylic acid tert-butyl esterYield 96.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 312751,4-DioxaneSolvent

Procedure

To 4-(3-methyl-5-nitropyridin-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylic acid tert-butyl ester (5.0 g) were added 1,4-dioxane (50 ml) and 10% palladium carbon (containing about 50% water, 2.0 g), stirred at room temperature for 9 hours under hydrogen atmosphere, then 10% palladium carbon (containing about 50% water, 1.5 g) was additionally added thereto, and stirred at 40° C. for 8.5 hours under hydrogen atmosphere. The reaction solution was filtered through Celite, and then the solvent was evaporated in vacuo to give 4-(5-amino-3-methylpyridin-2-yl)piperidine-1-carboxylic acid tert-butyl ester (4.4 g) as a yellow oil.

Workup

  1. stirringstirred at 40° C. for 8.5 hours under hydrogen atmosphere
  2. filtrationThe reaction solution was filtered through Celite
  3. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-51ae490fe4704833a6c42a417b7947ed
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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