Dimethylformamide → 3-Acetylsulfanyl-1-Boc-piperidine

HRID 468567노트

반응식

HRID 468567 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 547762383-Acetylsulfanyl-1-Boc-piperidine수율 47.1%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
95 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e062e35e7edc4d6e9f21f073138b0f4d
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08624033B2

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