Reaction #8239

Reaction equation

5(R)-[N-isoxazol-3-yl-N-(2,2,2-trichloroethyloxycarbonyl)-aminomethyl]-3-[3-fluoro-4-(1-formyl-1,2,5,6-tetrahydropyrid-4-yl)phenyl]oxazolidin-2-one

→

title compound

5(S)-Isoxazol-3-ylaminomethyl-3-(3-fluoro-4-(1-formyl-1,2,5,6 tetrahydropyrid-4-yl)phenyl)oxazolidin-2-one

Solvents

acetic acid

Conditions

Workup

1. 1
   FiltrationThe mixture was filtered through celite
2. 2
   Otherthe filtrate was evaporated
3. 3
   FiltrationThe residue was taken into ˜5% MeOH/CH2Cl2 (5 ml) with filtration of inorganic material

Procedure

To a stirred solution of 5(R)-[N-isoxazol-3-yl-N-(2,2,2-trichloroethyloxycarbonyl)-aminomethyl]-3-[3-fluoro-4-(1-formyl-1,2,5,6-tetrahydropyrid-4-yl)phenyl]oxazolidin-2-one (110 mg, 0.2 mM) in acetic acid (3 ml) was added zinc dust (130 mg, 2.0 mM). The mixture was held in an ultrasonic bath for 10 min. and then stirred vigorously for 48 hours under a nitrogen atmosphere at ambient temperature. The mixture was filtered through celite and the filtrate was evaporated. The residue was taken into ˜5% MeOH/CH2Cl2 (5 ml) with filtration of inorganic material and the title compound was isolated by MPLC (4% MEOH/CH2Cl2). It was obtained as a brittle glass on evaporation under high vacuum (22 mg, 28%).

Source