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

HRID 889063Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH2:11][CH:12]2[CH2:16][C:15](=[O:17])[N:14]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[CH2:13]2)[CH:10]=1)=[O:5])C.[OH-].[Na+]>CO.O>[O:17]=[C:15]1[N:14]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:25])[F:26])[CH:19]=2)[CH2:13][CH:12]([CH2:11][N:9]2[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]2)[CH2:16]1

Participants

Conditions

Temperature: 100 °C

Procedure

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).

Workup

temperatureThe reaction mixture was cooled
customMeOH was removed under reduced pressure
additiondiluted with water
washwashed with DCM
extractionThe acidified mixture was extracted with EtOAc (3×50 mL)
extractionthe combined extract
washwas washed with brine
dry with materialdried with Na2SO4
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-41c602a361844648959992b6775d9674
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252797B2

Reaction notes

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