Methyl iodide → HCID 57544970, compound

HRID 2355481Notes

Reaction equation

HRID 2355481 reaction equation
[OH:1][C:2]([CH3:19])([CH3:18])[CH2:3][C@H:4]1[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[N:5]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].[H-].[Na+].I[CH3:23]>C1COCC1>[CH3:23][O:1][C:2]([CH3:19])([CH3:18])[CH2:3][C@H:4]1[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[N:5]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57544854HCID 57544854, compound

Product 1

HCID 57544970HCID 57544970, compoundYield 122.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (S)-tert-butyl 4-(2-hydroxy-2-methylpropyl)-2,2-dimethyl-oxazolidine-3-carboxylate (0.93 g, 3.4 mmol) in anhydrous THF (8 mL), there was added NaH (60 wt % in mineral oil, 0.41 g, 10.2 mmol) followed by iodomethane (1.46 g, 10.2 mmol). The resulting mixture was stirred at rt until no starting material remained (˜5 h). The reaction was quenched by slow addition of water, the organic layer was separated, and aqueous layer was extracted with ether (2×5 mL). The combined organic layers were washed with 1 N aq HCl (5 mL), sat'd aq NaHCO3 (5 mL) and brine (5 mL), dried over Na2SO4 and concentrated to give crude (S)-tert-butyl 4-(2-methoxy-2-methylpropyl)-2,2-dimethyloxazolidine-3-carboxylate (1.2 g, quant.) which was used without purification. MS m/z 310 (M+Na+).

Workup

  1. custom(˜5 h)
  2. customThe reaction was quenched by slow addition of water
  3. customthe organic layer was separated
  4. extractionaqueous layer was extracted with ether (2×5 mL)
  5. washThe combined organic layers were washed with 1 N aq HCl (5 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8ead8af34ff248ca93d5172ea8741542
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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