Acetone → 1-[2-(5-Nitro-2-pentafluoroethylphenoxy)-ethyl]-pyrrolidine

Temperature

70 °C

A flask was charged with 5-nitro-2-pentafluoroethyl-phenol (3.67 g, 14.2 mmol), 1-(2-chloroethyl)pyrrolidine hydrochloride (9.71 g, 57.1 mmol), K2CO3 (7.9 g, 57.1 mmol), and acetone (20 mL). The reaction was heated at 70° C. for 3 days. The acetone evaporated from the reaction. No reaction was observed, so the organic material was recovered by extraction of water with EtOAc. The organic layer was dried with MgSO4, filtered and concentrated in vacuo. This crude mixture was dissolved in DMF (20 mL), combined with K2CO3 (5.9 g, 42.1 mmol) and heated to 70° C. for 24 h. The reaction mixture was cooled to RT, taken up in EtOAc and washed with 2 N NaOH, and brine. The organic layer was dried with MgSO4, filtered and concentrated in vacuo. The aqueous layer was acidified, extracted with EtOAc and dried with MgSO4, filtered, concentrated in vacuo and combined with the other portion. The title compound was purified by column chromatography using 0-10% MeOH in CH2Cl2.

1. customThe acetone evaporated from the reaction
2. customwas recovered by extraction of water with EtOAc
3. dry with materialThe organic layer was dried with MgSO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. dissolutionThis crude mixture was dissolved in DMF (20 mL)
7. temperatureheated to 70° C. for 24 h
8. temperatureThe reaction mixture was cooled to RT
9. washwashed with 2 N NaOH, and brine
10. dry with materialThe organic layer was dried with MgSO4
11. filtrationfiltered
12. concentrationconcentrated in vacuo
13. extractionextracted with EtOAc
14. dry with materialdried with MgSO4
15. filtrationfiltered
16. concentrationconcentrated in vacuo
17. customThe title compound was purified by column chromatography

ORD record

ord-13e4be4a046c4e3a841c1a9a54ffbc57

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07531553B2