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

HRID 2082339ノート

反応式

HRID 2082339 の反応式
[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]

参加物

5

反応物 1

HCID 12069550N-Boc-2-aminomethylpyridine

生成物 1

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

試薬・触媒・溶媒 3

HCID 345198Adams' catalyst触媒HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7300ba0cc9cb4f3e96e9723ba9fbc5bc
出典データセット
uspto-grants-1993_02
特許番号
US05189046

反応ノート

読み込み中…