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

HRID 1462980노트

반응식

HRID 1462980 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-edf70bdca1704367892a92a1a8366560
출처 데이터셋
uspto-grants-1984_07
특허 번호
US04461895

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