Tetrahydrofuran → 8-Methoxy-1,2,3,4-tetrahydroisoquinoline

HRID 228480ノート

反応式

HRID 228480 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:11](=O)[NH:10][CH2:9][CH2:8]2.C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][NH:10][CH2:9][CH2:8]2

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 129507458-methoxy-3,4-dihydroisoquinolin-1(2H)-oneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 129507478-Methoxy-1,2,3,4-tetrahydroisoquinoline収率 93%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Combine 8-Methoxy-3,4-dihydro-2H-isoquinolin-1-one (0.778 g, 4.40 mmol), THF (20 ml), and LiAlH4 (0.333 g, 8.8 mmol) at 0° C. under nitrogen atmosphere. After 30 minutes the reaction, reflux for 2 hours and then cool to room temperature. Quench the reaction by adding water and 1M NaOH at 0° C. and stirring for 12 hours at room temperature. Filter the reaction through celite and elute with THF. After concentrating the filtrate under reduced pressure, add the mixture to a 10 g SCX column pre-treated with 5% AcOH/MeOH. After rinsing several times with MeOH, elute the product using 1N NH3-MeOH followed by concentration under reduced pressure to afford 0.665 g, 4.07 mmol (93% yield) of the title compound as a tan oil: 1H NMR (500 MHz, CDCl3); 1.7-2.0 (1H, b s), 2.77 (2H, t, J=5.86), 3.09 (2H, t, J=5.86), 3.8 (3H, s), 3.95 (2H, s), 6.6-6.8 (2H, m), 7.0-7.15 (1H, m); TLC 5% MeOH: Ethyl acetate Rf:=0.1

後処理

  1. customat 0° C.
  2. customAfter 30 minutes the reaction
  3. temperaturereflux for 2 hours
  4. customQuench
  5. customthe reaction
  6. filtrationFilter
  7. customthe reaction through celite and
  8. washelute with THF
  9. concentrationAfter concentrating the filtrate under reduced pressure
  10. additionadd the mixture to a 10 g SCX column
  11. additionpre-treated with 5% AcOH/MeOH
  12. washAfter rinsing several times with MeOH
  13. washelute the product
  14. concentrationfollowed by concentration under reduced pressure

出典と根拠

ORDレコード
ord-224023eee2494b49938964df6cbc1131
出典データセット
uspto-grants-2009_07
特許番号
US07560463B2

反応ノート

読み込み中…