Sodium borohydride → 2-(3-fluorophenyl)pyrrolidine

To a stirred solution of 5-(3-fluoro-phenyl)-3,4-dihydro-2H-pyrrole (1.10 g, 6.74 mmol) in methanol (40 ml) was added at 0° C. sodium borohydride (0.51 g, 13.4 mmol) and the reaction mixture was stirred at RT for 1 h. Then additional sodium borohydride (0.25 g, 6.61 mmol) was added and stirring was continued for 1 h. The mixture was evaporated, dissolved in saturated NaHCO3-solution (70 ml) and extracted with dichloromethane (2×70 ml). The combined organic layers were washed with brine (70 ml), dried (MgSO4) and evaporated. The crude product was purified by column chromatography on silica gel (dichloromethane/MeOH/NH4OH 15:1:0.1) to give the product (0.77 g, 69%) as a colorless oil, MS: m/e=165 (M+).

1. stirringstirring
2. waitwas continued for 1 h
3. customThe mixture was evaporated
4. dissolutiondissolved in saturated NaHCO3-solution (70 ml)
5. extractionextracted with dichloromethane (2×70 ml)
6. washThe combined organic layers were washed with brine (70 ml)
7. dry with materialdried (MgSO4)
8. customevaporated
9. customThe crude product was purified by column chromatography on silica gel (dichloromethane/MeOH/NH4OH 15:1:0.1)

ORD record

ord-433d9dd8e2504b82994092988a61f437

Source dataset

uspto-grants-2001_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06284785B1