trans-Cinnamamide → HCID 66608832, 화합물

HRID 1529543

반응식

HRID 1529543 반응식
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C:9](=O)[CH:8](Br)[CH2:7]1)=[O:5])[CH3:2].[C:14]([NH2:24])(=[O:23])/[CH:15]=[CH:16]/[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C:9]2[N:24]=[C:14](/[CH:15]=[CH:16]/[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:23][C:8]=2[CH2:7]1)=[O:5])[CH3:2]

참가 물질

3

반응물 2

HCID 5273472trans-CinnamamideHCID 13799628Ethyl 3-bromo-4-oxopiperidine-1-carboxylate

생성물 1

HCID 66608832HCID 66608832, 화합물수율 27%

반응 조건

온도
125 °C

실험 절차

A mixture of 3-bromo-4-oxo-1-piperidinecarboxylic acid ethyl ester (13.5 g, 26.99 mmol) and trans-cinnamamide (3.0 g, 20.7 mmol) was supported in silica gel (48 g) and mechanically stirred at 125° C. for 60 hours. The product was eluted from the silica gel with a 7M solution of ammonia in MeOH (3×140 mL). The filtrate was evaporated in vacuo and the crude product was basified with a saturated solution of NaHCO3 and extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 20/80). The desired fractions were collected and the solvents evaporated in vacuo to yield 6,7-dihydro-2-[(E)-2-phenylethenyl]-oxazolo[5,4-c]pyridine-5(4H)-carboxylic acid ethyl ester (1.65 g, 27% yield) as an orange oil. C17H18N2O3 LCMS: Rt 2.91, m/z 299 [M+H]+ (using method, LC-MS Method 6)

후처리

  1. washThe product was eluted from the silica gel with a 7M solution of ammonia in MeOH (3×140 mL)
  2. customThe filtrate was evaporated in vacuo
  3. extractionextracted with DCM
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo
  8. customThe crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 20/80)
  9. customThe desired fractions were collected
  10. customthe solvents evaporated in vacuo

출처 및 근거

ORD 기록
ord-0686e2e6d88345aeaff8bb1450c3eb43
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090632B2

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