Triphenylphosphine → HCID 11530538, compound

Participants

Reaction Steps

Diisopropyl azodicarboxylate (0.396 mmol) was added dropwise to a solution of 3-(1,4-diazabicyclo[3.2.2]non-4-ylcarbonyl)-1,2-benzisothiazol-6-ol (0.359 mmol), cyclopropyl carbinol (0.432 mmol), and triphenylphosphine (0.541 mmol) in tetrahydrofuran (2.2 mL). The reaction mixture was maintained at rt for 16 h, and then the reaction mixture was concentrated. The residue was purified by chromatography using a gradient of 50/50 to 0/100 ethyl acetate/[(70/30/1) ethylacetate/methanol/ammonium hydroxide)]. The compound was further purified by preparative HPLC to provide the product in 39% yield. 1H NMR (CD3OD) δ 8.06 and 8.05 (two d, J=9.0 ea, 1H), 7.56 (d, J=1.8, 1H), 7.14 and 7.13 (two dd, J=8.7, 2.2 ea, 1H), 5.00 (m, 0.79H), 4.50 (m, 0.34H), 4.25 (t, J=5.6, 0.68H), 4.09 (t, J=5.6, 1.34H), 3.95 (d, J=6.9, 2H), 3.63 (t, J=5.7, 0.70H), 3.62-3.36 (m, 5H), 2.45-2.37 (m, 2H), 2.26-2.02 (two m, 2H), 1.37-1.27 (m, 1H), 0.69-0.62 (m, 2H), 0.42-0.37 (m, 2H); LC/MS (EI) tR3.91 min, m/z 358 (M++1).

Provenance & Evidence