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

HRID 1462980Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1462980
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-edf70bdca1704367892a92a1a8366560
Quelldatensatz
uspto-grants-1984_07
Patentnummer
US04461895

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