1,2,3,4-Tetrahydroisoquinoline → (R)-2-(oxiran-2-ylmethyl)-1,2,3,4-tetrahydroisoquinoline

HRID 2201993Notes

Reaction equation

HRID 2201993 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:18][C@H:19]1[CH2:21][O:20]1>CO>[O:20]1[CH2:21][C@H:19]1[CH2:18][N:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1

Participants

5

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 11430Potassium CarbonateHCID 2734062(-)-Epichlorohydrin

Product 1

HCID 30076569(R)-2-(oxiran-2-ylmethyl)-1,2,3,4-tetrahydroisoquinolineYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1,2,3,4-tetrahydroisoquinoline (1 g, 7.52 mmol) in MeOH (40 mL) was added K2CO3 (5.19 g, 37.6 mmol) under 0° C. After stirring for 30 minutes, (R)-2-(chloromethyl) oxirane (0.692 g, 7.52 mmol) was added the reaction. The mixture was then stirred at 0° C. overnight before filtration and washing of the solid by with MeOH. The solution was concentrated and the residue purified by column separation to give the title compound as a colorless oil (70% purity). This crude was used directly in the next step. LCMS (m/z): 190.1 (M+1).

Workup

  1. customthe reaction
  2. stirringThe mixture was then stirred at 0° C. overnight before filtration
  3. washwashing of the solid by with MeOH
  4. concentrationThe solution was concentrated
  5. customthe residue purified by column separation

Sources & evidence

ORD record
ord-3a66de56f30b445da65767dcee40d548
Source dataset
uspto-grants-2016_06
Patent number
US09365519B2

Reaction notes

Loading…