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Potassium Carbonate → 4-(4-Chloro-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester

HRID 504464
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HRID 504464 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].C([O-])([O-])=O.[K+].[K+].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27](OS(C)(=O)=O)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>CN(C=O)C>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([O:10][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:9][C:6]=2[CH:7]=[O:8])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

생성물 1

HCID 577501934-(4-Chloro-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester수율 78%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a mixture of 5-chloro-2-hydroxy-benzaldehyde (3.15 g, 20 mmol), KI (0.1 g) and K2CO3 (8.28 g, 60 mmol) in DMF (100 mL) was added 4-methanesulfonyloxy-piperidine-1-caboxylic acid tert-butyl ester (7.26 g, 26 mmol). The mixture was heated at 100° C. for 2 h, then cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was washed with 1N NaOH (30 mL), water, and dried over anhydrous Na2SO4, concentrated to give the title compound as white solid (Yield: 5.3 g, 78%).

후처리

  1. temperaturecooled to room temperature
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with 1N NaOH (30 mL), water
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-161b2d1793d5411798675f7de360f4de
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07776875B2

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