Sodium Hydroxide → 1-[5-Oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidin-3-ylmethyl]-1H-pyrazole-4-carboxylic acid

To a stirred solution of 1-[5-Oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidin-3-ylmethyl]-1H-pyrazole-4-carboxylic acid ethyl ester (2.6 g, 6.81 mmol) in 14 mL MeOH:H2O (3:11), NaOH (0.4 g, 10.5 mmol) was added at room temperature. The mixture was heated at 100° C. for 2 h. The reaction mixture was cooled; MeOH was removed under reduced pressure, diluted with water, washed with DCM and acidified with 1% HCl. The acidified mixture was extracted with EtOAc (3×50 mL) and the combined extract was washed with brine, dried with Na2SO4, evaporated under reduced pressure to give the title compound in 88% yield (2.1 g).

1. temperatureThe reaction mixture was cooled
2. customMeOH was removed under reduced pressure
3. additiondiluted with water
4. washwashed with DCM
5. extractionThe acidified mixture was extracted with EtOAc (3×50 mL)
6. extractionthe combined extract
7. washwas washed with brine
8. dry with materialdried with Na2SO4
9. customevaporated under reduced pressure

ORD record

ord-41c602a361844648959992b6775d9674

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08252797B2