Ethanol → (R)-3,4-dihydro-5-(2-oxiranylmethoxy)-1(2H)-isoquinolinone

HRID 1645919Notes

Reaction equation

HRID 1645919 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][C:7]2=[O:12].[C:13](=[O:16])([O-])[O-].[K+].[K+].[CH2:19](O)[CH3:20]>>[O:16]1[CH2:13][C@@H:19]1[CH2:20][O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][C:7]2=[O:12]

Participants

4

Reactant 3

HCID 702EthanolHCID 11430Potassium CarbonateHCID 132366635-Hydroxy-1,2,3,4-tetrahydroisoquinolin-1-one

Product 1

HCID 18649438(R)-3,4-dihydro-5-(2-oxiranylmethoxy)-1(2H)-isoquinolinone

Procedure

A mixture of 2.0 g (12.3 mmol) of 3,4-dihydro-5-hydroxy-1(2H)-isoquinolinone, 3.3 g (14.7 mmol) of (R)-glycidal tosylate and 2.03 g (14.7 mmol) of potassium carbonate in 100 ml of ethanol were refluxed until complete (as indicated by TLC). The reaction mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was dried and concentrated. The desired product, (R)-3,4-dihydro-5-(2-oxiranylmethoxy)-1(2H)-isoquinolinone, was obtained by chromatography; mp 161°-64° (Rotation=+12.5°).

Workup

  1. temperaturewere refluxed until complete (as indicated by TLC)
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between ethyl acetate and water
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b5d70f7ae0014fe18a1b9f5ed30e3dc2
Source dataset
uspto-grants-1993_01
Patent number
US05177075

Reaction notes

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