Methyl iodide → HCID 21027185, compound

HRID 623751Notes

Reaction equation

HRID 623751 reaction equation
[CH3:1][C:2]([CH3:14])([CH3:13])[CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[H-].[Na+].[CH3:17]I>CN(C=O)C>[CH3:1][C:2]([CH3:14])([CH3:13])[CH2:3][CH2:4][N:5]([CH3:17])[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20626548HCID 20626548, compound

Product 1

HCID 21027185HCID 21027185, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 3,3-dimethylbutylcarbamate (1.72 g, 8.56 mmol) in dry DMF (20 mL) was portionwise added 60% NaH in mineral oil (685 mg, 17.12 mmol) under a N2 atmosphere. After 30 min, MeI (2.68 mL, 42.8 mmol) was added dropwise with ice cooling. The mixture was stirred at room temperature for 2 d, poured in ice-H2O and extracted with Et2O (30 mL). The organic layer was dried (Na2SO4) and concentrated to yield the desired product (1.43 g, 63%, 80% purity) as a colourless oil.

Workup

  1. extractionextracted with Et2O (30 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9df281192966433f9d66e56db7c216f9
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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