Tetraethylammonium fluoride hydrate → (S)-tert-Butyl 2,2-dimethyl-4-(((R)-tetrahydro-2H-pyran-3-yl)methyl)oxazolidine-3-carboxylate

To a solution of (S)-tert-butyl 4-((R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(methylsulfonyloxy)pentyl)-2,2-dimethyloxazolidine-3-carboxylate (37.7 g, 74.2 mmol) in THF (1000 mL) was added tetraethylammonium fluoride hydrate (41 g, 185.5 mmol) in portions. The reaction mixture was stirred under reflux overnight. The mixture was diluted with EtOAc (1000 mL), washed with water (300 mL) and brine (500 mL). The organic phase was dried over Na2SO4, filtered and concentrated in vacuo to give the crude product, which was purified by column chromatography to afford (S)-tert-butyl 2,2-dimethyl-4-(((R)-tetrahydro-2H-pyran-3-yl)methyl)oxazolidine-3-carboxylate (12.0 g, 54%).

1. temperatureunder reflux overnight
2. washwashed with water (300 mL) and brine (500 mL)
3. dry with materialThe organic phase was dried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customto give the crude product, which
7. customwas purified by column chromatography

ORD 기록

ord-44bbb61d75a74dd183e061f195371f94

출처 데이터셋

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08580823B2