Borane;tetrahydrofuran → HCID 57991895, compound

Temperature

0 °C

To a stirred mixture of (2S,3S)-methyl 3-(4-(trifluoromethyl)phenyl)pyrrolidine-2-carboxylate (0.33 g, 1.21 mmol) in THF (5.0 mL) was added BH3-THF (12 mL, 12 mmol) at 0° C. The mixture was heated at reflux for 4 hours. The mixture was cooled to 0° C., the reaction carefully quenched with MeOH, and the mixture was evaporated in vacuo. The residue was diluted with saturated aqueous NaHCO3, water and extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated. The crude residue was purified by flash column chromatography (ISCO Combiflash system, eluting with a gradient from pure DCM to 5% MeOH in DCM) to provide ((2S,3S)-3-(4-(trifluoromethyl)phenyl)pyrrolidin-2-yl)methanol as a white solid (45 mg, 15%).

1. temperatureThe mixture was heated
2. temperatureat reflux for 4 hours
3. customthe reaction
4. customcarefully quenched with MeOH
5. customthe mixture was evaporated in vacuo
6. additionThe residue was diluted with saturated aqueous NaHCO3, water
7. extractionextracted with EtOAc (3×50 mL)
8. washThe combined organic layers were washed with brine
9. dry with materialdried over Na2SO4
10. concentrationconcentrated
11. customThe crude residue was purified by flash column chromatography (ISCO Combiflash system
12. washeluting with a gradient from pure DCM to 5% MeOH in DCM)

ORD record

ord-658d3f72d38645cc8e2307ec245228a9

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07919504B2