1-(2-Methylsulfanyl-ethyl)-3,4-dihydro-isoquinoline-3-carboxylic acid methyl ester → 1-(2-Methylsulfanyl-ethyl)-isoquinoline-3-carboxylic acid methyl ester

HRID 1845009Notes

Reaction equation

HRID 1845009 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([CH2:15][CH2:16][S:17][CH3:18])=[N:6]1)=[O:4]>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH2:15][CH2:16][S:17][CH3:18])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:4]

Participants

4

Reactant 1

HCID 669404581-(2-Methylsulfanyl-ethyl)-3,4-dihydro-isoquinoline-3-carboxylic acid methyl ester

Product 1

HCID 669404221-(2-Methylsulfanyl-ethyl)-isoquinoline-3-carboxylic acid methyl esterYield 29.1%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

1.297 g (7 mmol) of copper acetate was added to a solution of 923 mg (3.5 mmol) of 1-(2-methylsulfanyl-ethyl)-3,4-dihydro-isoquinoline-3-carboxylic acid methyl ester in 10 mL of dichloromethane, stirring at room temperature overnight. This reaction mixture was concentrated and purified by column chromatography on silica gel to give 266 mg (29%) of 1-(2-methylsulfanyl-ethyl)-isoquinoline-3-carboxylic acid methyl ester. LCMS: 262 (M+1)+.

Workup

  1. concentrationThis reaction mixture was concentrated
  2. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d9acd411093744f996919745feacb792
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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