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

HRID 2383020ノート

反応式

HRID 2383020 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11026Titanium isopropoxide触媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-5cc4ff23798e42878d55fc5c46635a82
出典データセット
uspto-grants-2012_09
特許番号
US08263607B2

反応ノート

読み込み中…