1,2,3,4-Tetrahydroisoquinoline → Ethyl (3,4-dihydro-1H-isoquinolin-2-yl)acetate

HRID 914986Notes

Reaction equation

HRID 914986 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.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(#N)C>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

5

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 2839036Ethyl (3,4-dihydro-1H-isoquinolin-2-yl)acetateYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 40 (1.33 g, 10.0 mmol) in acetonitrile (50 mL) were sequentially added potassium carbonate (5.53 g, 40.0 mmol) and ethyl bromoacetate (1.67 g, 10.0 mmol). The reaction mixture was stirred at room temperature overnight, then partitioned between EtOAc (200 mL) and water (150 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to give 90 (2.1 g, 99%).

Workup

  1. custompartitioned between EtOAc (200 mL) and water (150 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b880e24fa31744c98ec00b101a0a267e
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Reaction notes

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