4-(Trifluoromethyl)benzenesulfonyl chloride → HCID 178527338, compound

Participants

Reaction Steps

((4R)-4-cyclopropyl-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-6-yl)methanol (36) (627 mg, 3.50 mmol) and 4-trifluoromethylbenzenesulfonyl chloride (2.57 g, 10.5 mmol) were dissolved in pyridine (5 mL) and the resulting mixture was stirred at rt for 12 h. The reaction mixture was diluted with CH2Cl2 (10 mL) and washed with 1 N aq. HCl (10 mL). The aq. phase was separated and extracted once with CH2Cl2 (10 mL) and the combined organic phases were then dried (Na2SO4), filtered and concentrated under vacuum. The residue was dissolved in THF (5 mL) and 3 N aq. NaOH (3.5 mL) was added. The resulting mixture was stirred at rt for 18 h and was subsequently extracted with EtOAc. The organic phase was then dried (Na2SO4), filtered, concentrated under vacuum and purified by preparative HPLC to give ((4R)-4-cyclopropyl-5-(4-(trifluoromethyl)phenylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-6-yl)methanol (37) as a white solid. Retention time (min)=5.573, method [7], MS (m/z) 410.0 (M+Na)+.

Provenance & Evidence