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

HRID 1777086Notes

Reaction equation

HRID 1777086 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 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 522689Potassium Fluoride

Product 1

HCID 30076569(R)-2-(oxiran-2-ylmethyl)-1,2,3,4-tetrahydroisoquinolineYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 1,2,3,4-tetrahydroisoquinoline (10 g, 0.15 mol) in THF (100 mL) at 0° C. was added KF (22 g, 0.3 mmol). After 1 h, (S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (21.4 g, 0.17 mmol) was added and the resulting solution was stirred at 22° C. for 16 h. The solid was removed by filtration and washed with THF. The solution was concentrated and the crude compound was used for next step without further purification (15 g, Yield 53%). LCMS (m/z): 190.1 (M+1).

Workup

  1. customThe solid was removed by filtration
  2. washwashed with THF
  3. concentrationThe solution was concentrated
  4. customthe crude compound was used for next step without further purification (15 g, Yield 53%)

Sources & evidence

ORD record
ord-7b822fc967494de8860637542b031930
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

Loading…