Methyl iodide → HCID 66976182, compound

HRID 1022777Notes

Reaction equation

HRID 1022777 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:15]([CH2:16][OH:17])[O:14][CH2:13][CH2:12][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].[Na+].[CH3:27]I>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:15]([CH2:16][O:17][CH3:27])[O:14][CH2:13][CH2:12][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydride2×HCID 66975659HCID 66975659, compound

Product 1

HCID 66976182HCID 66976182, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (6RS,7SR)-6-(3,4-dichlorophenyl)-7-(hydroxymethyl)-1,4-oxazepane-4-carboxylate (150 mg) in THF (3 mL) was added sodium hydride (24 mg), and the mixture was stirred at room temperature for 15 min. To this solution was added methyl iodide (85 mg), and the mixture was stirred for 2 hr. Furthermore, sodium hydride (24 mg) was added, and the mixture was stirred at room temperature for 4 hr. To the reaction solution was added ice water, and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (151 mg).

Workup

  1. stirringthe mixture was stirred for 2 hr
  2. stirringthe mixture was stirred at room temperature for 4 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1a465708f9424f549e5aa6e743697a45
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

Loading…