1-(tert-Butoxycarbonyl)piperidine-4-carboxamide → Tert-butyl 4-{4-[4-(methylsulfanyl)phenyl]-1,3-oxazol-2-yl}piperidine-1-carboxylate

HRID 716709노트

반응식

HRID 716709 반응식
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)=O.[C:13]([CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)(=[O:15])[NH2:14]>CN1C(=O)N(C)CCC1>[CH3:12][S:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:14]=[C:13]([CH:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)[O:15][CH:2]=2)=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 27356461-(tert-Butoxycarbonyl)piperidine-4-carboxamideHCID 27375232-Bromo-1-(4-methylsulfanylphenyl)ethanone

생성물 1

HCID 71207840Tert-butyl 4-{4-[4-(methylsulfanyl)phenyl]-1,3-oxazol-2-yl}piperidine-1-carboxylate수율 25.1%

시약·촉매·용매 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-용매

반응 조건

온도
145 °C

실험 절차

2-Bromo-1-[4-(methylsulfanyl)phenyl]ethanone (5 g, 19.15 mmol) and tert-butyl 4-carbamoylpiperidine-1-carboxylate (4.37 g, 19.15 mmol) were dissolved in DMPU (40.8 mL) and heated to 145° C. for 15 min. The resulting solution was then cooled to room temperature, partitioned between aqueous LiCl and ethyl acetate. The combined organics were dried over sodium sulfate and concentrated in vacuo. The resulting crude oil was purified using silica gel chromatography (300 g, using 20-80% ethyl acetate in hexane gradient) to yield 1.8 g of the desired product as a yellow oil. LCMS (M+1)=375.40

후처리

  1. temperatureThe resulting solution was then cooled to room temperature
  2. custompartitioned between aqueous LiCl and ethyl acetate
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting crude oil was purified

출처 및 근거

ORD 기록
ord-5c00385fa3474bff98ae15ed7735f3ed
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193697B2

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