Tert-butyl 4-(methylsulfonyl)piperidine-1-carboxylate → tert-Butyl 4-(acetylthio)piperidine-1-carboxylate

HRID 390994ノート

反応式

HRID 390994 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11](S(C)(=O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:18]([O-:21])(=[S:20])[CH3:19].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([S:20][C:18](=[O:21])[CH3:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 22504298Tert-butyl 4-(methylsulfonyl)piperidine-1-carboxylateHCID 23700354HCID 23700354、化合物

生成物 1

HCID 22494773tert-Butyl 4-(acetylthio)piperidine-1-carboxylate収率 64.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A mixture of 4-methanesulfonyl-piperidine-carboxylic acid tert-butyl ester (2.82 g), sodium thioacetate (2.31 g) and DMF (40 ml) was stirred at 60° C. After 4 hours the reaction mixture was cooled and partitioned between ethyl acetate and brine. The combined organics were dried (MgSO4) and the solvents removed in vacuo. The resulting crude mixture was purified by flash chromatography to yield 4-acetylsulfanyl-piperidine-1-carboxylic acid tert-butyl ester (1.8 g).

後処理

  1. temperatureAfter 4 hours the reaction mixture was cooled
  2. custompartitioned between ethyl acetate and brine
  3. dry with materialThe combined organics were dried (MgSO4)
  4. customthe solvents removed in vacuo
  5. customThe resulting crude mixture was purified by flash chromatography

出典と根拠

ORDレコード
ord-9d16d40425434ea8a3f4369e6c0e7620
出典データセット
uspto-grants-2013_02
特許番号
US08383620B2

反応ノート

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