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

HRID 2202002Notes

Reaction equation

HRID 2202002 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.[F-].[K+].[N+](C1C=C(S(O[CH2:26][C@H:27]2[CH2:29][O:28]2)(=O)=O)C=CC=1)([O-])=O>C1COCC1>[O:28]1[CH2:29][C@@H:27]1[CH2:26][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 146513Benzenesulfonic acid, 3-nitro-, (2R)-2-oxiranylmethyl esterHCID 522689Potassium Fluoride

Product 1

HCID 30076572(S)-2-(oxiran-2-ylmethyl)-1,2,3,4-tetrahydroisoquinolineYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,2,3,4-tetrahydroisoquinoline (5 g, 7.52 mmol) in THF (100 mL) was added KF (8.57 g, 150.4 mmol) at 0° C. (R)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (10.7 g, 41.4 mmol) was added to the reaction in 1 h. The solution was stirred at room temperature overnight. The solid was removed by filtration and washed with THF. The solution was then concentrated and the residue used for next step without further purification (11.3 g Yield 80%). LCMS (m/z): 190.1 (M+1).

Workup

  1. additionwas added to the reaction in 1 h
  2. customThe solid was removed by filtration
  3. washwashed with THF
  4. concentrationThe solution was then concentrated
  5. customthe residue used for next step without further purification (11.3 g Yield 80%)

Sources & evidence

ORD record
ord-cecfdf763f6d42faa456fbf3dc9c0fbf
Source dataset
uspto-grants-2016_06
Patent number
US09365519B2

Reaction notes

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