1,2,3,4-Tetrahydroisoquinoline → 2-[(Oxiran-2-yl)methyl]-1,2,3,4-tetrahydroisoquinoline

HRID 880333Notes

Reaction equation

HRID 880333 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+].Br[CH2:18][CH:19]1[CH2:21][O:20]1>CC#N>[O:20]1[CH2:21][CH: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 18430Epibromohydrin

Product 1

HCID 167845312-[(Oxiran-2-yl)methyl]-1,2,3,4-tetrahydroisoquinolineYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
21 °C

Procedure

To a stirring solution of 1,2,3,4-tetrahydroisoquinoline (15 g, 0.11 mol) in MeCN (100 mL) at 0° C. was added K2CO3 (30.7 g, 0.23 mol), then 2-(bromomethyl)oxirane (17 g, 0.12 mol) added slowly over a period of 1 h. After the addition the solution was stirred at 21° C. for 12 h. The resulting solid was then removed by filtration and washed with MeCN and the combined organic filtrate was concentrated under reduced pressure to give the crude product. This residue was used into next step without further purification (17 g, Yield: 78%). LCMS (m/z): 190.1 (M+1).

Workup

  1. additionAfter the addition the solution
  2. customThe resulting solid was then removed by filtration
  3. washwashed with MeCN
  4. concentrationthe combined organic filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7c03bea1c8364d09b81fd24b56375f4f
Source dataset
uspto-grants-2015_03
Patent number
US08993555B2

Reaction notes

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