1-[Bis(hydroxymethyl)-methyl]-6,7-dimethoxy-3,4-dihydroisoquinoline → 2-(6,7-Dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-propane-1,3-diol

HRID 542196Notes

Reaction equation

HRID 542196 reaction equation
[OH:1][CH2:2][CH:3]([CH2:18][OH:19])[C:4]1[C:13]2[C:8](=[CH:9][C:10]([O:16][CH3:17])=[C:11]([O:14][CH3:15])[CH:12]=2)[CH2:7][CH2:6][N:5]=1>C(O)C.[H][H].[Pt]>[OH:1][CH2:2][CH:3]([CH2:18][OH:19])[CH:4]1[C:13]2[C:8](=[CH:9][C:10]([O:16][CH3:17])=[C:11]([O:14][CH3:15])[CH:12]=2)[CH2:7][CH2:6][NH:5]1

Participants

5

Reactant 1

HCID 136966801-[Bis(hydroxymethyl)-methyl]-6,7-dimethoxy-3,4-dihydroisoquinoline

Product 1

HCID 136966832-(6,7-Dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-propane-1,3-diolYield 95%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 702EthanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

0.01 mole (2.65 g) of 1-[bis(hydroxymethyl)-methyl]-6,7-dimethoxy-3,4-dihydroisoquinoline is dissolved in 50 ml of ethanol, and the mixture is reduced in hydrogen atmosphere, in the presence of a 10% platinum-on-activated carbon catalyst, under normal conditions. After uptake of the calculated amount of hydrogen (1 to 2 hours), the catalyst is filtered off and the filtrate is evaporated to yield the aimed compound in crystalline form.

Workup

  1. filtrationAfter uptake of the calculated amount of hydrogen (1 to 2 hours), the catalyst is filtered off
  2. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-a895f5a26e684c1d88d3ab1f84cfa431
Source dataset
uspto-grants-1987_04
Patent number
US04656179

Reaction notes

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