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

HRID 381422

反応式

HRID 381422 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
105 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e2579ce9059c4d15bee54582b6413b74
出典データセット
uspto-grants-2001_10
特許番号
US06306880B1

関連ノート

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