Acetic Acid → cis-3-(Boc-amino)-5-methylpiperidine

HRID 571713Notes

Reaction equation

HRID 571713 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[N:6][CH:7]=1.CC(O)=O>[Pt]>[CH3:1][C@@H:2]1[CH2:7][NH:6][CH2:5][C@H:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3]1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 21300389tert-butyl N-(5-methyl-3-pyridyl)carbamate

Product 1

HCID 58386822cis-3-(Boc-amino)-5-methylpiperidine

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Procedure

A Parr bottle was charged with tert-butyl 5-methylpyridin-3-ylcarbamate (365 mg, 1.75 mmol) and AcOH (10 mL, 0.17 mol). Nitrogen was bubbled through the mixture for several minutes with stirring before 5% Pt/C (365 mg, 0.027 mol) was added, and the bottle was placed under an atmosphere of hydrogen (60 psi) for 24 h. The mixture was filtered and the solvent concentrated in vacuo to afford the title intermediate as an oil, which was used without further purification.

Workup

  1. customNitrogen was bubbled through the mixture for several minutes
  2. additionwas added
  3. filtrationThe mixture was filtered
  4. concentrationthe solvent concentrated in vacuo

Sources & evidence

ORD record
ord-b516faf86b614a5090383822fc37a2aa
Source dataset
uspto-grants-2015_05
Patent number
US09029359B2

Reaction notes

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