Sodium borohydride → Tert-butyl 5-cyclopropyl-2-fluoro-4-((4-hydroxybicyclo-[4.1.0]heptan-1-yl)methoxy)benzoate

Participants

Reaction Steps

To a solution of tert-butyl 5-cyclopropyl-2-fluoro-4-((4-oxobicyclo[4.1.0]heptan-1-yl)methoxy)benzoate (0.63 g, 1.70 mmol) was dissolved in 1,2- dimethoxyethane (5 mL), sodium borohydride (0.13 g, 3.40 mmol) was added. The reaction mixture was stirred for 0.5 hour and quenched with slow addition of water (5 mL) followed by ethyl acetate (10 mL). To this reaction mixture was added concentrated hydrochloride (37%, 1.0 mL) and stirred for 10 minutes. The organic layer was separated and the solvent was concentrated in vacuo to afford the title compound as a solid (0.13 g, 19%): 1H NMR (300 MHz, CDCl3) (7.36 (d, J=8.5 Hz, 1H), 6.40 (d, J=12.7 Hz, 1H), 3.78 (d, J=9.2 Hz, 1H), 3.62 (d, J=9.4 Hz, 1H), 2.40-2.30 (m, 4H), 2.20-2.07 (m, 2H), 1.99-1.92 (m, 1H), 1.53 (s, 9H), 1.42-1.33 (m, 1H), 1.29-1.09 (m, 2H), 0.89-0.82 (m, 4H), 0.76-0.71 (m, 1H, 0.65-0.60 (m, 2H), 0.47 (t, J=5.3 Hz, 1H); MS (ES+) m/z 377.2 (M+1).

Provenance & Evidence