Potassium Iodide → (+)-2-Cyclopropylmethyl-7-hydroxy-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline

HRID 1462980ノート

反応式

HRID 1462980 の反応式
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][CH:9]2[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([OH:21])[CH:14]=2)=[CH:4][C:3]=1[O:22][CH3:23].C(=O)(O)[O-].[Na+].[I-].[K+].Cl[CH2:32][CH:33]1[CH2:35][CH2:34]1>C(O)C>[CH:33]1([CH2:32][N:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][C:2]([OH:1])=[C:3]([O:22][CH3:23])[CH:4]=3)[CH:9]2[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([OH:21])[CH:14]=2)[CH2:35][CH2:34]1

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 80013(Chloromethyl)cyclopropaneHCID 443766norreticulineHCID 516892Sodium Bicarbonate

生成物 1

HCID 13109062(+)-2-Cyclopropylmethyl-7-hydroxy-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

16.2 g. (48.9 mmol) (-)-7-Hydroxy-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline, 8.2 g. (100 mmol) sodium bicarbonate and 500 mg. potassium iodide are dissolved in 200 ml. anhydrous ethanol and mixed with 4.5 ml. (4.44 g., 49 mmol) chloromethylcyclopropane. The reaction mixture is boiled under reflux for 40 hours in an inert gas atmosphere. The usual working up and chromatographic separation of unreacted starting material on silica gel with chloroform as elution agent gives (+)-2-cyclopropylmethyl-7-hydroxy-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline; m.p. 70°-81° C. (recrystallised from methanol/diethyl ether/hexane).

後処理

  1. temperatureunder reflux for 40 hours in an inert gas atmosphere
  2. customchromatographic separation
  3. washas elution agent

出典と根拠

ORDレコード
ord-edf70bdca1704367892a92a1a8366560
出典データセット
uspto-grants-1984_07
特許番号
US04461895

反応ノート

読み込み中…