N-Boc-2-aminomethylpyridine → tert-butyl N-((piperidin-2-yl)methyl)carbamate

HRID 2082339Notes

Reaction equation

HRID 2082339 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.C(O)(=O)C.O=[Pt]=O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][NH:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 12069550N-Boc-2-aminomethylpyridine

Product 1

HCID 2756031tert-butyl N-((piperidin-2-yl)methyl)carbamateYield 80.6%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 108 g (0.518 mol) of 2-[N-(tert-butoxycarbonyl)aminomethyl]pyridine in 500 mL of ethanol and 50 mL of glacial acetic acid was hydrogenated over 5 grams of PtO2 at 55 psi for 36 hours employing a Parr apparatus. The mixture was cautiously filtered through Celite® and solvent was removed at reduced pressure. The crude material was dissolved in ethyl acetate, washed with 2N aqueous NaOH, water, brine, and dried over MgSO4. Solvent was removed at reduced pressure and the resulting solid was recrystallized from ethyl acetate/hexane to provide 89.5 grams (80%) of 2-[N-(tert-butoxycarbonyl)aminomethyl]piperidine as a white solid. Mp. 93° C.

Workup

  1. filtrationThe mixture was cautiously filtered through Celite® and solvent
  2. customwas removed at reduced pressure
  3. dissolutionThe crude material was dissolved in ethyl acetate
  4. washwashed with 2N aqueous NaOH, water, brine
  5. dry with materialdried over MgSO4
  6. customSolvent was removed at reduced pressure
  7. customthe resulting solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-7300ba0cc9cb4f3e96e9723ba9fbc5bc
Source dataset
uspto-grants-1993_02
Patent number
US05189046

Reaction notes

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