Tetrabutylammonium Fluoride → 4-(5-Oxazol-5-yl-furo[2,3-c]pyridin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

Tetrabutylammonium fluoride (1 mol/L in tetrahydrofuran; 1.5 mL) is added to a solution of 4-[5-(2-triisopropylsilanyl-oxazol-5-yl)-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (0.31 g) in tetrahydrofuran (6 mL) chilled in an ice bath. The cooling bath is removed and the solution is stirred at room temperature for 2 h. Water is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are dried (Na2SO4) and concentrated. The residue is purified by HPLC on reversed phase (methanol/water) to give the title compound. LC (method 4): tR=1.66 min; Mass spectrum (ESI+): m/z=370 [M+H]+.

Provenance & Evidence