Water → tert-Butyl 7-methoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 636944Notes

Reaction equation

HRID 636944 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([OH:18])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:19](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 10562576Tert-butyl 7-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

Product 1

HCID 54125269tert-Butyl 7-methoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 2.5 g of 7-hydroxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester and 2.8 g of powdered potassium carbonate in 25 mL of dry N,N-dimethylformamide was added methyl iodide (0.94 mL) at 5° C. Stirring was continued for 24 hours at room temperature. Water was added and the mixture was extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried (sodium sulfate) and the solvent was removed in vacuo. The crude product (2.7 g; oil) was used in the next step without further purification. EI-MS: 263 (M+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried (sodium sulfate)
  4. customthe solvent was removed in vacuo
  5. customThe crude product (2.7 g; oil) was used in the next step without further purification

Sources & evidence

ORD record
ord-13a66f6f833a4b1bb17930e5a403e061
Source dataset
uspto-grants-2001_02
Patent number
US06194409B1

Reaction notes

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