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

HRID 1095067노트

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HRID 1095067 반응식
[I:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>CN(C)C=O.C(OCC)(=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]([I:1])=[CH:9][C:6]=2[CH:7]=[O:8])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 2526125-IodosalicylaldehydeHCID 157347131-(tert-Butoxycarbonyl)-4-(p-toluenesulfonyloxy)piperidine

생성물 1

HCID 577432744-(2-Formyl-4-iodo-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester수율 84%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

To a solution of 5-iodosalicylaldehyde (3 g, 12.1 mmol) (Aldrich) in N,N-dimethylformamide (20 mL) was added anhydrous K2CO3 (5 g, 36.3 mmol), and 4-(toluene-4-sulfonyloxy)-piperidine-1-carboxylic acid tert-butyl ester (5.4 g, 18.1 mmol, ASTATECH). The reaction mixture was heated at 60° C. for 18 h. The mixture was cooled to room temperature, diluted with ethyl acetate, washed with water. The organic layer was separated, the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with water, brine, dried over MgSO4, and concentrated to give crude 4-(2-formyl-4-iodo-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester as a yellow oil (Yield 4.38 g, 84%).

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with water
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washwashed with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-cc2c979b317247feb5c24eb3d60a086a
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08134001B2

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