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

HRID 1399848Notes

Reaction equation

HRID 1399848 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>C(#N)C>[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 62,878.602%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
25 °C

Procedure

To a stirring solution of 1,2,3,4-tetrahydroisoquinoline (13.4 g, 0.1 mmol) in acetonitrile (200 mL) was added anhydrous K2CO3 (20.7 g, 0.15 mol), then 2-(bromomethyl)oxirane (13.7 g, 0.1 mol) in MeCN (20 ml) was added drop wise to the reaction. After addition, the solution was stirred at 25° C. for 4 h until completion of the reaction was observed by LCMS. The solvent was evaporated and the residue purified with column chromatography to afford the desired product as a colorless oil (11.9 g, 80% purity, 50% yield).

Workup

  1. customwise to the reaction
  2. additionAfter addition
  3. customThe solvent was evaporated
  4. customthe residue purified with column chromatography

Sources & evidence

ORD record
ord-70a47eb09f214ac2a4b8d6c069cb5816
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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