1,2-Dichloroethane → Tert-butyl 4-[(5-chloro-2-hydroxypiperidin-3-yl)amino]piperidine-1-carboxylate

HRID 1026548노트

반응식

HRID 1026548 반응식
ClCCCl.[NH2:5][C:6]1[C:7]([OH:13])=[N:8][CH:9]=[C:10]([Cl:12])[CH:11]=1.O=[C:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.O>[Cl:12][CH:10]1[CH2:9][NH:8][CH:7]([OH:13])[CH:6]([NH:5][CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)[CH2:11]1

참가 물질

7

반응물 4

HCID 111,2-DichloroethaneHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate2회HCID 5049666Sodium triacetoxyborohydride2회HCID 178507679HCID 178507679, 화합물

생성물 1

HCID 68006279Tert-butyl 4-[(5-chloro-2-hydroxypiperidin-3-yl)amino]piperidine-1-carboxylate수율 62.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a 1,2-dichloroethane suspension (177 ml) of 3-amino-5-chloropyridin-2-ol (8.85 g) and tert-butyl 4-oxopiperidine-1-carboxylate (24.4 g) was added sodium triacetoxyborohydride (26.0 g), followed by stirring under heating at reflux for 4 hours. Tert-butyl 4-oxopiperidine-1-carboxylate (12.4 g) and sodium triacetoxyborohydride (13.7 g) were further added, and stirred under heating at reflux for 2 hours. After the reaction solution was brought back to room temperature, water and dichloromethane were added, and the solution was separated. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford tert-butyl 4-[(5-chloro-2-hydroxypiperidin-3-yl)amino]piperidine-1-carboxylate (12.7 g).

후처리

  1. temperatureunder heating
  2. temperatureat reflux for 4 hours
  3. stirringstirred
  4. temperatureunder heating
  5. temperatureat reflux for 2 hours
  6. customwas brought back to room temperature
  7. customthe solution was separated
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-e808f8802edc46c28c0443fc3386bf8b
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729095B2

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