Methyl iodide → HCID 66975157, compound

HRID 1022533Notes

Reaction equation

HRID 1022533 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]2[O:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH:12]2[CH2:25][OH:26])[CH:7]=[CH:8][C:9]=1[Cl:10].[CH3:27]I>C1COCC1>[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]2[O:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:13][CH:12]2[CH2:25][O:26][CH3:27])[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66975761HCID 66975761, compound

Product 1

HCID 66975157HCID 66975157, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of sodium hydride (10.5 mg) in THF (1 mL) was added a solution of tert-butyl (6RS,7RS)-7-(3,4-dichlorophenyl)-6-(hydroxymethyl)-1,4-oxazepane-4-carboxylate (65.7 mg) in THF (1 ml), and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added methyl iodide (49.7 mg), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate. The diluted solution was washed with distilled water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (58.4 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with ethyl acetate
  4. washThe diluted solution was washed with distilled 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-dfdd583a34fe4a4f91687ae35354474a
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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