Tetrabutylammonium Fluoride → HCID 67135302, compound

Participants

Reaction Steps

To a solution of methyl (2S,4R)-1-(3-chloro-5-(5-(2-(methoxymethyl)-2′-methylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)-4-(tert-butyldimethylsilyloxy)-pyrrolidine-2-carboxylate (0.118 g; 0.18 mmol) in THF (2 mL) was added a solution of tetrabutylammonium fluoride (1.0 M in THF; 0.36 mL; 0.36 mmol). The reaction mixture was stirred at ambient temperature for 18 hours. The mixture was diluted with DCM and water and poured through a hydrophobic frit. The solvent was evaporated in vacuo and the residue was purified by flash chromatography on silica, eluting with iso-hexane/EtOAc (100% iso-hexane to 50%/50% iso-hexane/EtOAc) to afford the title product (0.085 g; 88%). 1H NMR (CDCl3, 400 MHz) δ 8.81 (1H, d, J=2 Hz), 8.40 (1H, d, J=1.2 Hz), 8.26 (1H, d, J=1.6 Hz), 8.15-8.13 (1H, m), 7.34-7.24 (4H, m), 7.14-7.12 (1H, m), 5.01 (1H, t, J=8 Hz), 4.66 (1H, s), 4.34-4.30 (1H, m), 4.22-4.21 (2H, m), 4.02-3.99 (1H, m), 3.74 (3H, s), 3.33 (3H, s), 2.38 (1H, m), 2.21-2.14 (1H, m), 2.08 (3H, s), 1.76 (1H, d, J=3.6 Hz).

Provenance & Evidence