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

HRID 1467987

반응식

HRID 1467987 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-6b98d450d34d4947afe804c798f92a1c
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000175B2

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