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

HRID 1462980Notes

Reaction equation

HRID 1462980 reaction equation
[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

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 80013(Chloromethyl)cyclopropaneHCID 44376613168-51-9HCID 516892Sodium Bicarbonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-edf70bdca1704367892a92a1a8366560
Source dataset
uspto-grants-1984_07
Patent number
US04461895

Reaction notes

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