(R)-tert-Butyl 2-Methyl-4-(6-nitropyridin-3-yl)piperazine-1-carboxylate → (R)-tert-Butyl 4-(6-aminopyridin-3-yl)-2-methylpiperazine-1-carboxylate

HRID 1026412Notes

Reaction equation

HRID 1026412 reaction equation
[CH3:1][C@@H:2]1[CH2:7][N:6]([C:8]2[CH:9]=[N:10][C:11]([N+:14]([O-])=O)=[CH:12][CH:13]=2)[CH2:5][CH2:4][N:3]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[H][H]>CO.[C].[Pd]>[NH2:14][C:11]1[N:10]=[CH:9][C:8]([N:6]2[CH2:5][CH2:4][N:3]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:2]([CH3:1])[CH2:7]2)=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 49840311(R)-tert-Butyl 2-Methyl-4-(6-nitropyridin-3-yl)piperazine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 49840989(R)-tert-Butyl 4-(6-aminopyridin-3-yl)-2-methylpiperazine-1-carboxylateYield 88.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 108a (1.0 g, 3.1 mmol) in methanol (15 mL) was added 10% palladium carbon (100 mg). The mixture was stirred at room temperature under the atmosphere of hydrogen for overnight. At the end of reaction, it was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with DCM/MeOH (10:1, UV) to afford 108b as a brown solid (800 mg, 88%). LCMS: [M+H]+ 293

Workup

  1. customAt the end of reaction, it
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography
  5. washeluting with DCM/MeOH (10:1, UV)

Sources & evidence

ORD record
ord-9af5c836275d47eabc387fac4d538b49
Source dataset
uspto-grants-2014_05
Patent number
US08729072B2

Reaction notes

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