Water → Tert-butyl 4-(1-methoxy-1-methylethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

HRID 1162309Notes

Reaction equation

HRID 1162309 reaction equation
[OH:1][C:2]([CH:5]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])([CH3:4])[CH3:3].[CH3:19]I.[H-].[Na+].O>CN(C)C=O>[CH3:19][O:1][C:2]([CH:5]1[CH2:9][O:8][C:7]([CH3:10])([CH3:11])[N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 23138373tert-Butyl 4-(1-hydroxy-1-methylethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Product 1

HCID 23138231Tert-butyl 4-(1-methoxy-1-methylethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl 4-(1-hydroxy-1-methylethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (Y. Yonezaw et al., Synthesis, 634-636 (2000); 2.6 g) and methyl iodide (1.2 ml) were dissolved in dimethylformamide (20 ml). Sodium hydride (0.59 g) and n-tetrabutyl iodide ammonium (0.72 g) were added thereto at 0° C., and mixed at room temperature for 2.5 days. To the reaction mixture was added water, and extracted with diethyl ether. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain the title compound as a pale yellow oil (2.5 g, 95%).

Workup

  1. additionat 0° C., and mixed at room temperature for 2.5 days
  2. extractionextracted with diethyl ether
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-da73497ab5b44b118937888734e42696
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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