2,6-Dichloropyridine → Tert-butyl 4-[(6-chloropyridin-2-yl)oxy]piperidine-1-carboxylate

HRID 1467987

反応式

HRID 1467987 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20](Cl)[N:19]=1>C1COCC1>[Cl:17][C:18]1[N:19]=[C:20]([O:14][CH:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]2)[CH:21]=[CH:22][CH:23]=1

参加物

5

反応物 3

HCID 169892,6-DichloropyridineHCID 24758Sodium hydrideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

生成物 1

HCID 21906058Tert-butyl 4-[(6-chloropyridin-2-yl)oxy]piperidine-1-carboxylate収率 48%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

To a stirred solution of 4-Hydroxy-piperidine-1-carboxylic acid tert-butyl ester (1.63 g, 8.1 mmol) in THF (20 mL), NaH (0.40 g, 10.1 mmol)) was added and stirred at 60° C. for 0.5 h. 2,6-dichloropyridine (1.0 g, 6.75 mmol) was added and stirred at room temperature for 3-4-h. The reaction was quenched with water and extracted with ethyl acetate. The organic layer was concentrated in vacuo and the resultant residue was purified by flash column chromatography to yield tert-butyl 4-((6-chloropyridin-2-yl)oxy)piperidine-1-carboxylate as a pale yellow solid (0.98 g, 48%); MS: 335.1 (M+23)

後処理

  1. stirringstirred at room temperature for 3-4-h
  2. customThe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic layer was concentrated in vacuo
  5. customthe resultant residue was purified by flash column chromatography

出典と根拠

ORDレコード
ord-6b98d450d34d4947afe804c798f92a1c
出典データセット
uspto-grants-2015_04
特許番号
US09000175B2

関連ノート

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