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

HRID 2271539Notes

Reaction equation

HRID 2271539 reaction equation
[CH3:1][N:2]([CH:10]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][N:16]=2)[CH2:11]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[H][H]>C1COCC1.[Pd]>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([N:12]2[CH2:13][CH2:14][CH:10]([N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:6])([CH3:7])[CH3:8])[CH2:11]2)=[N:16][CH:17]=1

Participants

5

Reactant 2

HCID 58386085Tert-butyl methyl(1-(5-nitropyridin-2-yl)pyrrolidin-3-yl)carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 57652013Tert-butyl (1-(5-aminopyridin-2-yl)pyrrolidin-3-yl)(methyl)carbamateYield 100.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl methyl(1-(5-nitropyridin-2-yl)pyrrolidin-3-yl)carbamate (1.02 g, 3.2 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 (940 mg, 100%) as a red oil. ESI MS m/z 293 [C15H24N4O2+H]+

Workup

  1. filtrationfiltered through celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-8508ab781227482292cbc28fc48be5ee
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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