p-Fluoronitrobenzene → HCID 68696157, compound

Temperature

0 °C

The crude 3-(3-Fluoro-pyrrolidin-1-yl)-propan-1-ol (assumed 3.06 mmol) was dissolved in THF (8 mL) and was cooled to 0° C. The 0° C. solution was treated consecutively with KOtBu (1.5 g, 13.5 mmol) then 4-fluoronitrobenzene (423.3 mg, 3 mmol). The resulting reaction mixture was allowed to warm to room temperature and stir for an additional 4.5 h. The reaction mixture was quenched with the addition of ice water (50 mL) followed by extraction with EtOAc (75 mL). The organics were subsequently washed with room temperature H2O (75 mL), then saturated NaHCO3 (aq) (75 mL), and finally with brine (75 mL). The organics then were dried over anhydrous sodium sulfate, decanted and concentrated in vacuo to yield crude 3-Fluoro-1-[3-(4-nitro-phenoxy)-propyl]-pyrrolidine (660 mg) as a yellow oil. This material was carried on without further purification.

1. customThe resulting reaction mixture
2. temperatureto warm to room temperature
3. customThe reaction mixture was quenched with the addition of ice water (50 mL)
4. extractionfollowed by extraction with EtOAc (75 mL)
5. washThe organics were subsequently washed with room temperature H2O (75 mL)
6. dry with materialThe organics then were dried over anhydrous sodium sulfate
7. customdecanted
8. concentrationconcentrated in vacuo

ORD record

ord-311856f481414d098697137369f2e7da

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07749530B2