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

HRID 1026548ノート

反応式

HRID 1026548 の反応式
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

参加物

7

反応物 4

HCID 111,2-DichloroethaneHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate2 回HCID 5049666Sodium triacetoxyborohydride2 回HCID 178507679HCID 178507679、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e808f8802edc46c28c0443fc3386bf8b
出典データセット
uspto-grants-2014_05
特許番号
US08729095B2

反応ノート

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