HCID 9879568, compound → HCID 9879646, compound

Participants

Reaction Steps

A mixture of (5R)-(−)-3-[4-(3,6-dihydro-2H-pyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide (EXAMPLE 9, Step 2, 200 mg, 0.653 mmol) and 10% palladium-on-carbon (139 mg, 0.131 mmol) in methanol (26 mL) is shaken under a 40 psi hydrogen atmosphere on a Parr apparatus for 5 h. The catalyst is then removed by filtration through a pad of Celite, and the filtrate is concentrated under reduced pressure and chromatographed on a Flash 40S 40 g silica gel (32–63 μm) cartridge, eluting with a gradient of methanol/methylene chloride (2/98–3/97). Pooling and concentration of those fractions with an Rf=0.37 by TLC (methanol/chloroform, 2×5/95) gives the title compound, mp 153–156° C.; MS (ESI−) for C15H17N2O4F m/z 307 (M−H)−; [α]25D=−21 (c 0.87, DMSO).

Provenance & Evidence