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

HRID 2082339노트

반응식

HRID 2082339 반응식
[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]

참가 물질

5

반응물 1

HCID 12069550N-Boc-2-aminomethylpyridine

생성물 1

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

시약·촉매·용매 3

HCID 345198Adams' catalyst촉매HCID 176Acetic Acid용매HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7300ba0cc9cb4f3e96e9723ba9fbc5bc
출처 데이터셋
uspto-grants-1993_02
특허 번호
US05189046

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