1-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine → tert-Butyl 4-(acetylthio)piperidine-1-carboxylate

HRID 381422

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HRID 381422 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11](OS(C)(=O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:19]([O-:22])(=[S:21])[CH3:20].[K+]>CN(C)C=O.C(OCC)(=O)C>[C:19]([S:21][CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]1)(=[O:22])[CH3:20]

참가 물질

5

반응물 2

HCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 23670855Potassium ethanethioate

생성물 1

HCID 22494773tert-Butyl 4-(acetylthio)piperidine-1-carboxylate수율 905.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
105 °C

실험 절차

In 40 ml of dimethylformamide were dissolved 4.12 g (14.7 mmol) of 1-(tert-butoxycarbonyl)-4-(methanesulfonyloxy)piperidine, and 2.53 g (2.21 mmol) of potassium thioacetate were added to the solution, followed by stirring of the resulting mixture at 105° C. for 4 hours under nitrogen atmosphere. After cooling, the reaction mixture was diluted with ethyl acetate and washed with water and then a saturated aqueous NaCl solution, followed by evaporation of the solvent. The thus obtained residue was subjected to silica gel column chromatography and the fractions eluted with a mixed solvent of hexane-ethyl acetate (5:1) were collected to obtain 5.19 g (yield: 81%) of the title compound as an oil.

후처리

  1. additionwere added to the solution
  2. temperatureAfter cooling
  3. washwashed with water
  4. customa saturated aqueous NaCl solution, followed by evaporation of the solvent
  5. washthe fractions eluted with a mixed solvent of hexane-ethyl acetate (5:1)
  6. customwere collected

출처 및 근거

ORD 기록
ord-e2579ce9059c4d15bee54582b6413b74
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06306880B1

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