Methyl iodide → HCID 118939124, compound

HRID 524013Notes

Reaction equation

HRID 524013 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH:16]([OH:18])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:19][CH2:20][CH:21]3[CH2:23][CH2:22]3)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:26]I>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH:16]([O:18][CH3:26])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:19][CH2:20][CH:21]3[CH2:22][CH2:23]3)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1179988792(1H)-Isoquinolinecarboxylic acid, 6-(cyclopropylmethoxy)-3,4-dihydro-4-hydroxy-, 1,1-dimethylethyl ester

Product 1

HCID 118939124HCID 118939124, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 200 mg (0.626 mmol) 6-cyclopropylmethoxy-4-hydroxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (example XLIII.1) in 3 mL THF are added 30 mg (0.69 mmol) NaH (55%) and stirred at r.t. for 30 min. Then 35 μL (0.56 mmol) methyl iodide are added and the reaction mixture is stirred at 80° C. over night. The reaction mixture is quenched by the addition of water and extracted three times with EtOAc. The organic layers are combined, dried over MgSO4, filtered and the solvent is removed in vacuo.

Workup

  1. stirringthe reaction mixture is stirred at 80° C. over night
  2. customThe reaction mixture is quenched by the addition of water
  3. extractionextracted three times with EtOAc
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-00ae0c3cdd484ce3b04ae04b4801c5ef
Source dataset
uspto-grants-2016_05
Patent number
US09340510B2

Reaction notes

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