Methyl iodide → (4R)-4,5-Dihydro-2-(methylthio)-4-thiazolemethanol

To a mixture solution of 4.88 g of 4(R)-hydroxymethyl-2-mercapto-1,3-thiazoline [Compound (5)] and 22.8 ml of diisopropylethylamine in 65 ml of dry methanol was added 14.00 g of methyl iodide under refluxing condition, and the reaction mixture was refluxed for hour. After removal of the solvent under reduced pressure, the resulting residue was dissolved in ethyl acetate and the organic layer was washed with saturated sodium bicarbonate solution, water and saturated saline solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and the resulting residue was purified by silica gel column chromatography (chloroform-acetone) to give 3.14 g (59%) of 4(R)-hydroxymethyl-2-methylthio-1,3-thiazoline [Compound (6)].

1. temperatureunder refluxing condition
2. temperaturethe reaction mixture was refluxed for hour
3. customAfter removal of the solvent under reduced pressure
4. dissolutionthe resulting residue was dissolved in ethyl acetate
5. washthe organic layer was washed with saturated sodium bicarbonate solution, water and saturated saline solution
6. dry with materialdried over magnesium sulfate
7. customThe solvent was removed under reduced pressure
8. customthe resulting residue was purified by silica gel column chromatography (chloroform-acetone)

ORD record

ord-2e57b04df3084e9f98c0f822bd41f0c2

Source dataset

uspto-grants-1996_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05534510