trans-Cinnamamide → HCID 66608832、化合物

HRID 1529543

反応式

HRID 1529543 の反応式
[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]

参加物

3

反応物 2

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

生成物 1

HCID 66608832HCID 66608832、化合物収率 27%

反応条件

温度
125 °C

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-0686e2e6d88345aeaff8bb1450c3eb43
出典データセット
uspto-grants-2015_07
特許番号
US09090632B2

関連ノート

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