3-Chloro-2-methyl-1-propene → (+)-7-Hydroxy-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-(2-methylprop-2-enyl)-1,2,3,4-tetrahydroisoquinoline

HRID 1462979Notes

Reaction equation

HRID 1462979 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+].Cl[CH2:30][C:31]([CH3:33])=[CH2:32]>C(O)C>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([CH2:32][C:31]([CH3:33])=[CH2:30])[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]

Participants

5

Reactant 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 44376613168-51-9HCID 516892Sodium Bicarbonate

Product 1

HCID 20452308(+)-7-Hydroxy-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-(2-methylprop-2-enyl)-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.7 g. (18.07 mmol) (-)-7-Hydroxy-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline and 3.7 g. (44 mmol) sodium bicarbonate in 120 ml. ethanol are mixed with 1.76 ml. (1.64 g., 18,07 mmol) 3-chloro-2-methylprop-1-ene. The mixture is allowed to react for 30 minutes at ambient temperature and thereafter for 3 hours at 80° C., while stirring. The usual working up and chromatographic purification on silica gel with chloroform as elution agent gives (+)-7-hydroxy-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-(2-methylprop-2-enyl)-1,2,3,4-tetrahydroisoquinoline in the form of a TLC-uniform yellowish foam.

Workup

  1. customto react for 30 minutes at ambient temperature
  2. customchromatographic purification on silica gel with chloroform
  3. washas elution agent

Sources & evidence

ORD record
ord-ed99e0ff79c541c089904488ee81aead
Source dataset
uspto-grants-1984_07
Patent number
US04461895

Reaction notes

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