Tetrabutylammonium Fluoride → 3-(1H-indol-5-yl)-azetidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

3-(1-Triisopropylsilanyl-1H-indol-5-yl)-azetidine-1-carboxylic acid tert-butyl ester (1.1 g, 64% purity, 1.63 mmol) was dissolved in THF (20 ml). Tetrabutylammonium fluoride (3.25 ml, 1 molar solution in THF) was added and the reaction mixture was stirred for 5 minutes at room temperature. The reaction mixture was concentrated, and the residue was dissolved in H2O (50 ml) and diethyl ether (50 ml). The crude product was purified by silica gel chromatography with dichloromethane as eluent, yielding the purified product (275 mg, 51% for 2 steps).

Provenance & Evidence