Dimethylformamide → 3-Acetylsulfanyl-1-Boc-piperidine

HRID 468567ノート

反応式

HRID 468567 の反応式
CN(C)C=O.[C:6]([N:13]1[CH2:18][CH2:17][CH2:16][CH:15](OS(C)(=O)=O)[CH2:14]1)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[C:24]([O-:27])(=[S:26])[CH3:25].[K+]>O>[C:6]([N:13]1[CH2:18][CH2:17][CH2:16][CH:15]([S:26][C:24](=[O:27])[CH3:25])[CH2:14]1)([O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:7]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 568122N-Boc-3-mesyloxypiperidineHCID 23670855Potassium ethanethioate

生成物 1

HCID 547762383-Acetylsulfanyl-1-Boc-piperidine収率 47.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
95 °C

実験手順

2.7 l of dimethylformamide are placed in a reactor under inert atmosphere. 251.4 g of N-BOC-3(R,S)-methylsulfonyloxy-piperidine are added with warming. At an internal temperature of 50° C. 256.8 g of potassium thioacetate are added at once. After stirring for 90 min at 95° C. the reaction mixture is transferred into a reactor filled with 4 l of water. 4.2 l of petroleum ether are added. After vigorous stirring for 5 minutes the aqueous phase is removed. After readdition of water the pH is adjusted to >8 with sodium hydroxide. The organic phase is separated, washed with water and treated with active charcoal. The solution is evaporated to dryness. After flash chromatography on silica with petroleum ether, toluene, and ethyl acetate and concentration of the product containing solution crystallization occurs on cooling and 110 g of N-BOC-3(R,S)-acetylthio-piperidine are obtained.

後処理

  1. temperaturewith warming
  2. customAt an internal temperature of 50° C
  3. customis transferred into a reactor
  4. stirringAfter vigorous stirring for 5 minutes the aqueous phase
  5. customis removed
  6. customThe organic phase is separated
  7. washwashed with water
  8. additiontreated with active charcoal
  9. customThe solution is evaporated to dryness
  10. additionAfter flash chromatography on silica with petroleum ether, toluene, and ethyl acetate and concentration of the product containing
  11. customsolution crystallization
  12. temperatureon cooling

出典と根拠

ORDレコード
ord-e062e35e7edc4d6e9f21f073138b0f4d
出典データセット
uspto-grants-2014_01
特許番号
US08624033B2

反応ノート

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