Borane;tetrahydrofuran → 3-(4-Chloro-phenyl)-2-(2-chloro-phenyl)-5-isopropyl-2,4,5,6-tetrahydro-pyrrolo[3,4-c]pyrazole

Participants

Reaction Steps

A solution of 3-(4-chloro-phenyl)-2-(2-chloro-phenyl)-5-isopropyl-4,5-dihydro-2H-pyrrolo[3,4-c]pyrazol-6-one 3A-1 (7 mg, 0.018 mmol) and BH3THF (166 ml, 166 mmol) was stirred at room temperature for 1 hour and at 50° C. for 17 hours. After the reaction mixture was cooled to room temperature, MeOH (5 ml) was added. The reaction mixture was heated under reflux for 2 h, cooled to room temperature, and concentrated in vacuo. The residue was diluted with 4 M HCl/dioxanes (1 ml) and concentrated under vacuum. The residue was dissolved in CH2Cl2 and hexanes were added to precipitate 8A-1 as a colorless solid (2 mg, 27%): +APCI MS (M+H) 372.5; 1H NMR (CD3OD): δ 7.59–7.43 (m, 4H), 7.38 (d, 2H), 7.20 (d, 2H), 4.80–4.65 (m, 2H), 3.91–3.82 (m, 1H), 3.68–3.55 (m, 2H), 1.52 (d, 6H).

Provenance & Evidence