Methyl iodide → HCID 57982626, compound

HRID 2360191Notes

Reaction equation

HRID 2360191 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3][CH2:2]1.I[CH3:17].[H-].[Na+].[NH4+].[Cl-]>CN(C)C=O.C(OCC)(=O)C>[CH3:17][N:8]([CH2:7][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)[C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 45092209tert-Butyl ((tetrahydro-2H-pyran-4-yl)methyl)carbamate

Product 1

HCID 57982626HCID 57982626, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl N-(4-tetrahydropyranylmethyl)carbamate (610 mg, 2.8 mmol) and iodomethane (805 mg, 5.6 mmol) in 6.0 mL of N,N-dimethylformamide was added sodium hydride (60%, 227 mg, 5.6 mmol) under ice-cooled conditions. After the reaction mixture was stirred at room temperature overnight, the solution was added with saturated NH4Cl aqueous solution, and diluted with ethyl acetate. The separated organic layer was washed with brine, and dried over Na2SO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 70/30) to obtain the title compound (607 mg, 95%).

Workup

  1. temperaturecooled conditions
  2. washThe separated organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 70/30)

Sources & evidence

ORD record
ord-29b3d5d6a51a4e5783fc6404da97bdde
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

Loading…