tert-butyl (3S)-3-methyl-4-(6-nitropyridin-3-yl)piperazine-1-carboxylate → (3S)-tert-Butyl 4-(6-Aminopyridin-3-yl)-3-methylpiperazine-1-carboxylate

HRID 1185036Notes

Reaction equation

HRID 1185036 reaction equation
[CH3:1][C@@H:2]1[N:7]([C:8]2[CH:9]=[N:10][C:11]([N+:14]([O-])=O)=[CH:12][CH:13]=2)[CH2:6][CH2:5][N:4]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:3]1>[Pd].C(O)C>[NH2:14][C:11]1[N:10]=[CH:9][C:8]([N:7]2[CH2:6][CH2:5][N:4]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:3][C@@H:2]2[CH3:1])=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 86683728tert-butyl (3S)-3-methyl-4-(6-nitropyridin-3-yl)piperazine-1-carboxylate

Product 1

HCID 86683730(3S)-tert-Butyl 4-(6-Aminopyridin-3-yl)-3-methylpiperazine-1-carboxylateYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 500-mL bottle was purged with nitrogen and charged with 105a (5.8 g, 18 mmol), 10% palladium on carbon (50% wet, 2.0 g) and ethanol (200 mL). It was evacuated, charged with hydrogen gas, and stirred for 16 h at room temperature. The hydrogen was then removed in vacuo and replaced with nitrogen. The catalyst was removed by filtration through a pad of CELITE® and the filtrate concentrated under reduced pressure to afford 105b as a brown solid (4.9 g, 96%). LCMS: [M+H]+ 293

Workup

  1. customA 500-mL bottle was purged with nitrogen
  2. customIt was evacuated
  3. additioncharged with hydrogen gas
  4. customThe hydrogen was then removed in vacuo
  5. customThe catalyst was removed by filtration through a pad of CELITE®
  6. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-ff8639fcd7a44a599acf205009ce8585
Source dataset
uspto-grants-2014_03
Patent number
US08669251B2

Reaction notes

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