Water → HCID 178524821, compound

Participants

Reaction Conditions

Reaction Steps

trans-1-(4-Hydroxy-cyclohexyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (62.3 mg, 0.203 mmol, prepared in Example 71, Step 1) was dissolved in methanol (0.3 mL). Lithium hydroxide (7.1 mg, 0.297 mmol) and water (0.3 mL) were added and the mixture was heated at 80° C. for 1 hour. After cooling to room temperature, the methanol was removed in vacuo. Tetrahydrofuran was added and removed in vacuo to insure complete removal of methanol. The residue was diluted with water and acidified with 6N HCl. Solid initially precipitated out of solution but quickly went to an oil/gum. The mixture was extracted with methylene chloride two times. The two organic phases were combined, washed with water, dried over sodium sulfate and concentrated to give trans-1-(4-hydroxy-cyclohexyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid (35.8 mg; 63%). Mass spectrum: m/z: 277.1 (M−H).

Provenance & Evidence