1-Cyclohexene-1-carboxaldehyde → N-(cyclohexa-1-en-1-ylmethyl)-2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanamine

HRID 2383020노트

반응식

HRID 2383020 반응식
[CH:1]1([CH:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][CH2:9][N:8]2[C:17](=[O:20])[CH2:18][NH2:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:21]1([CH:27]=O)[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]=1>C(Cl)Cl.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[C:21]1([CH2:27][NH:19][CH2:18][C:17]([N:8]2[CH2:9][CH2:10][C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:7]2[CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[O:20])[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]=1

참가 물질

5

반응물 2

HCID 51845401-Cyclohexene-1-carboxaldehydeHCID 593965892-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanamine

생성물 1

HCID 67537633N-(cyclohexa-1-en-1-ylmethyl)-2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanamine수율 62.6%

시약·촉매·용매 2

HCID 11026Titanium isopropoxide촉매HCID 6344Dichloromethane용매

실험 절차

2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanamine (695 mg) was dissolved in methylene chloride (12 mL), and titanium tetraisopropoxide (1.1 mL) and 1-cyclohexene-1-carboaldehyde (309 mg) were added thereto, followed by stirring at room temperature for 3 hours. Thereafter, the solvent was evaporated, and MeOH (15 mL) and then sodium cyanotrihydroborate (190 mg) were added to the mixture, followed by stirring for 14 hours. The solvent was evaporated, and water and EtOAc were added to the mixture. The mixture was filtered through celite and extracted with EtOAc. The extract was washed with saturated brine and then dried over magnesium sulfate. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography (chloroform-MeOH) to obtain N-(cyclohexa-1-en-1-ylmethyl)-2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanamine (585 mg).

후처리

  1. customThereafter, the solvent was evaporated
  2. additionMeOH (15 mL) and then sodium cyanotrihydroborate (190 mg) were added to the mixture
  3. stirringby stirring for 14 hours
  4. customThe solvent was evaporated
  5. additionwater and EtOAc were added to the mixture
  6. filtrationThe mixture was filtered through celite
  7. extractionextracted with EtOAc
  8. washThe extract was washed with saturated brine
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent was evaporated
  11. customthe resulting residue was purified by silica gel column chromatography (chloroform-MeOH)

출처 및 근거

ORD 기록
ord-5cc4ff23798e42878d55fc5c46635a82
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263607B2

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