Methyl iodide → HCID 69205970, compound

HRID 901951Notes

Reaction equation

HRID 901951 reaction equation
[H-].[Na+].[N:3]1([C:13]([C:15]2[CH:16]=[C:17]([CH:27]=[CH:28][CH:29]=2)[CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1.I[CH3:31].S([O-])(O)(=O)=O.[K+]>CN(C=O)C>[CH3:31][N:19]([CH2:18][C:17]1[CH:27]=[CH:28][CH:29]=[C:15]([C:13]([N:3]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6][CH2:5][CH2:4]2)=[O:14])[CH:16]=1)[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 11152801HCID 11152801, compound

Product 1

HCID 69205970HCID 69205970, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.91 g, 60% dispersion in oil, 23 mmol) was added to a solution of tert-butyl N-(3-(1,2,3,4-tetrahydroquinoline-1-carbonyl)benzyl)carbamate (8.0 g, 22 mmol) in DMF under nitrogen, while cooling in an ice/water bath. Allowed to warm to room temperature over 45 min. The mixture was cooled in an ice/water bath and iodomethane (9.8 g, 68 mmol) was added dropwise. Allowed to warm to room temperatue and stirred for 5 h. 0.3N Potassium hydrogen sulphate was added and the mixture was extracted with EtOAc. The organic phase was washed with water, dried over sodium sulphate and evaporated. Chromatography (30% EtOAc, 70% 60-80 petroleum ether) afforded tert-butyl N-methyl-N-(3-(1,2,3,4-tetrahydroquinoline-1-carbonyl)benzyl)carbamate (7.7 g, 93%) as a yellow gum.

Workup

  1. temperaturewhile cooling in an ice/water bath
  2. temperatureThe mixture was cooled in an ice/water bath
  3. temperatureAllowed to warm to room temperatue
  4. extractionthe mixture was extracted with EtOAc
  5. washThe organic phase was washed with water
  6. dry with materialdried over sodium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-8fd3262dc9d54e65b30f9c517e1e6269
Source dataset
uspto-grants-2008_04
Patent number
US07365065B2

Reaction notes

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