Tert-butyl methyl(1-(5-nitropyridin-2-yl)piperidin-3-yl)carbamate → Tert-butyl (1-(5-aminopyridin-2-yl)piperidin-3-yl)(methyl)carbamate

HRID 2271541Notes

Reaction equation

HRID 2271541 reaction equation
[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][N:17]=2)[CH2:11]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[H][H]>C1COCC1.[Pd]>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([N:12]2[CH2:13][CH2:14][CH2:15][CH:10]([N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:6])([CH3:7])[CH3:8])[CH2:11]2)=[N:17][CH:18]=1

Participants

5

Reactant 2

HCID 71646997Tert-butyl methyl(1-(5-nitropyridin-2-yl)piperidin-3-yl)carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 86692851Tert-butyl (1-(5-aminopyridin-2-yl)piperidin-3-yl)(methyl)carbamateYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl methyl(1-(5-nitropyridin-2-yl)piperidin-3-yl)carbamate (1.03 g, 3.1 mmol) in THF (50 mL) was added Pd/C (10 wt. %, 500 mg). The reaction mixture was stirred under 1 atm of hydrogen for 16 h, filtered through celite and concentrated to afford the desired product (902 mg, 96%) as a red oil. ESI MS m/z 307 [C16H26N4O2+H]+

Workup

  1. filtrationfiltered through celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-00a4af87799e4633b9cb8d9411b8f8a3
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

Loading…