tert-butyl (3R)-3-methyl-4-(6-nitro-3-pyridyl)piperazine-1-carboxylate → (R)-tert-Butyl 4-(6-Aminopyridin-3-yl)-3-methylpiperazine-1-carboxylate

HRID 1843217Notes

Reaction equation

HRID 1843217 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].CO>[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 86683716tert-butyl (3R)-3-methyl-4-(6-nitro-3-pyridyl)piperazine-1-carboxylate

Product 1

HCID 86683717(R)-tert-Butyl 4-(6-Aminopyridin-3-yl)-3-methylpiperazine-1-carboxylateYield 81.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 250-mL flask was purged with nitrogen and charged with 115a (1.5 g, 4.6 mmol), 10% palladium on carbon (50% wet, 200 mg), and methanol (70 mL). It was evacuated, charged with hydrogen gas, and stirred at room temperature for 10 h. The hydrogen was then evacuated and nitrogen was charged into the flask. The catalyst was removed by filtration through a pad of Celite and the filtrate was concentrated under reduced pressure to afford 115b (1.1 g, 81%) as a brown solid. MS-ESI: [M+H]+ 293

Workup

  1. customA 250-mL flask was purged with nitrogen
  2. customIt was evacuated
  3. additioncharged with hydrogen gas
  4. customThe hydrogen was then evacuated
  5. additionnitrogen was charged into the flask
  6. customThe catalyst was removed by filtration through a pad of Celite
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-61a6b216213e479481805d1174e7e1ba
Source dataset
uspto-grants-2015_02
Patent number
US08946213B2

Reaction notes

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