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

HRID 880259Notes

Reaction equation

HRID 880259 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-b3fefb6ee04841b5ba132e405aa431ed
Source dataset
uspto-grants-2015_03
Patent number
US08993555B2

Reaction notes

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