Water → tert-Butyl 3-fluoro-4-oxoazepane-1-carboxylate

The product from Step A was dissolved in DMSO (200 mL) and H2O (8.29 g, 460 mmol) followed by addition of LiCl (19.5 g, 460 mmol). The solution was warmed to 125° C. and the mixture was stirred overnight. The mixture was cooled to ambient temperature and partitioned between EtOAc (2.5 L) and water:brine (1:1, 2.0 L). The mixture was filtered through activated charcoal over Celite, which was washed with EtOAc, forming visible layers. The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography (10 to 80% EtOAc/hexanes) providing 4.5 g (21%) of the product as a thick pale orange oil.

1. temperatureThe mixture was cooled to ambient temperature
2. custompartitioned between EtOAc (2.5 L) and water:brine (1:1, 2.0 L)
3. filtrationThe mixture was filtered through activated charcoal over Celite, which
4. washwas washed with EtOAc
5. customforming visible layers
6. dry with materialThe organic layer was dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe crude product was purified by column chromatography (10 to 80% EtOAc/hexanes)

ORD-Eintrag

ord-10973f0bb61d4162831682d42d17b84a

Quelldatensatz

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08575145B2