Water → Tert-butyl 5-cyclopropyl-2-fluoro-4-((4-oxobicyclo[4.1.0]heptan-1-yl)methoxy)benzoate

Participants

Reaction Steps

To a solution of tert-butyl 5-cyclopropyl-2-fluoro-4-(spiro[bicyclo[4.1.0]heptane-3,2′-[1,3]dioxolan]-6-ylmethoxy)benzoate (0.61 g, 1.86 mmol) in tetrahydrofuran (2.0 mL) was added water (2.0 mL) followed by trifluoroacetic acid (0.75 g, 6.56 mmol). The reaction solution was stirred at ambient temperature for 16 hours. The reaction mixture was diluted with ethyl acetate (20 mL), washed with a solution of aqueous sodium hydroxide (2.0 mL, 3 M). The organic layer was separated and concentrated in vacuo to afford the title compound as a colorless gum (0.63 g, quant.): 1H NMR (300 MHz, CDCl3) δ 7.36 (d, J=8.4 Hz, 1H), 6.43 (d, J=12.6 Hz, 1H), 3.91 (d, J=9.3 Hz, 1H), 3.71 (d, J=9.3 Hz, 1H), 2.72 (dd, J=18.4, 5.4 Hz, 1H), 2.56-2.32 (m, 4H), 2.20-2.07 (m, 2H), 1.99-1.92 (m, 1H), 1.53 (s, 9H), 1.21-0.79 (m, 5H), 0.70 (t, J=5.3 Hz, 1H), 0.63-0.58 (m, 2H); MS (ES+) m/z 397.2 (M+23).

Provenance & Evidence