tert-Butyl (6-methylpyridin-3-yl)carbamate → tert-butyl N-(6-methylpiperidin-3-yl)carbamate

HRID 1942490Notes

Reaction equation

HRID 1942490 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1>C(O)(=O)C.C(O)C.[Pt](=O)=O>[CH3:1][CH:2]1[NH:7][CH2:6][CH:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 23090429tert-Butyl (6-methylpyridin-3-yl)carbamate

Product 1

HCID 42609251tert-butyl N-(6-methylpiperidin-3-yl)carbamateYield 86.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst2×HCID 18476134Acetic acid ethanolSolvent

Procedure

To a solution of tert-butyl (6-methylpyridin-3-yl)carbamate (9.00 g) in a mixture of acetic acid-ethanol (1:1, 100 ml) was added platinum (IV) oxide (900 mg), and the mixture was stirred under hydrogen pressure (0.4 MPa) at room temperature for 9 hours. To the mixture was further added platinum (IV) oxide (2.0 g), and the mixture was stirred for 10 hours. The reaction mixture was filtered on celite, and thereto was added toluene. The mixture was concentrated under reduced pressure, and to the residue was added a 5% aqueous potassium carbonates solution. The mixture was extracted with chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to give a crude product (8.03 g) of the title compound as a colorless oil.

Workup

  1. stirringthe mixture was stirred for 10 hours
  2. filtrationThe reaction mixture was filtered on celite
  3. additionwas added toluene
  4. concentrationThe mixture was concentrated under reduced pressure
  5. additionto the residue was added a 5% aqueous potassium carbonates solution
  6. extractionThe mixture was extracted with chloroform
  7. washthe organic layer was washed with a saturated aqueous sodium chloride solution
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e5ebbba9be5f4e7fb438e646c06b1716
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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