Hydrazine hydrate (1:1) → (5S)-5-(aminomethyl)-3-(3-fluorophenyl)-1,3-oxazolidin-2-one

A solution of phthalimide 110 (3.0 g, 8.82 mmol) in ethanol (EtOH, 30 mL) was treated with hydrazine monohydrate (2.20 g, 2.2 mL, 44.12 mmol, 5.0 equiv) at 25° C., and the resulting reaction mixture was warmed to reflux for 2 h. White precipitates formed as the reaction mixture was refluxed. When TLC and HPLC showed the reaction was complete, the reaction mixture was cooled to room temperature before being quenched with H2O (20 mL). The aqueous solution was then extracted with CH2Cl2 (3×40 mL), and the combined organic extracts were washed with H2O (2×20 mL) and saturated aqueous NaCl (20 mL), dried over MgSO4, and concentrated in vacuo. The residue was further dried in vacuo to afford the desired (5S)-5-aminomethyl-3-(3-fluoro-phenyl)-oxazolidin-2-one 111 (1.79 g, 96.6% yield) as a white powder. This product was directly used in the subsequent reactions without further purification. C10H11FN2O2, LCMS (EI) m/e 211 (M++H).

1. customthe resulting reaction mixture
2. temperaturewas warmed
3. temperatureto reflux for 2 h
4. customWhite precipitates
5. customformed as the reaction mixture
6. temperaturewas refluxed
7. custombefore being quenched with H2O (20 mL)
8. extractionThe aqueous solution was then extracted with CH2Cl2 (3×40 mL)
9. washthe combined organic extracts were washed with H2O (2×20 mL) and saturated aqueous NaCl (20 mL)
10. dry with materialdried over MgSO4
11. concentrationconcentrated in vacuo
12. customThe residue was further dried in vacuo

ORD record

ord-4ad0569bb2a741bda5253ab937eb887e

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08324398B2