反应详情

To a solution of (S)-4-(2-hydroxy-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (200 mg) in THF (5 ml) at room temperature were added sequentially tetrabutylammonium iodide (15 mg) and sodium hydride (35 mg, 60% dispersion in mineral oil). After stirring the mixture for 5 min at room temperature, benzyl bromide (0.10 ml) was added dropwise and stirring was continued for a further 16 h. The mixture was quenched by addition of saturated aq. ammonium chloride solution (3 ml), diluted with water, and extracted twice with diethyl ether. The combined organic phases were dried over sodium sulphate, filtered, and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (SiO2; heptane/EtOAc) to yield (S)-4-(2-benzyloxy-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester as a colourless oil (199 mg, 73%); MS (ISP): 336.3 ([M+H]+).

1. stirringstirring
2. waitwas continued for a further 16 h
3. customThe mixture was quenched by addition of saturated aq. ammonium chloride solution (3 ml)
4. additiondiluted with water
5. extractionextracted twice with diethyl ether
6. dry with materialThe combined organic phases were dried over sodium sulphate
7. filtrationfiltered
8. concentrationthe filtrate was concentrated in vacuo
9. customThe residue was purified by column chromatography (SiO2; heptane/EtOAc)