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

HRID 1399812Notes

Reaction equation

HRID 1399812 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 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a stirred solution of 1,2,3,4-tetrahydroisoquinoline (2.0 g, 7.52 mmol) in 25 mL CH3CN was added K2CO3 (1.25 g, 9.02 mmol) and the solution stirred at room temperature for 5 min. 2-(Bromomethyl)oxirane (1.03 g, 7.52 mmol) in MeCN (25 mL) was added drop wise over a 20 min period and the reaction mixture stirred at room temperature for 12 h. The mixture was then filtered and the filtrate was concentrated to yield a residue which was purified by column chromatography (EA/PE=1/1 to pure EA) to give the compound as a colorless oil (500 mg, 75% purity). And used directly in the next step. LCMS (m/z): 190 (M+1).

Workup

  1. stirringthe reaction mixture stirred at room temperature for 12 h
  2. filtrationThe mixture was then filtered
  3. concentrationthe filtrate was concentrated
  4. customto yield a residue which
  5. customwas purified by column chromatography (EA/PE=1/1 to pure EA)

Sources & evidence

ORD record
ord-803bff9c4664476c93adb43497ee3433
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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