Tetrabutylammonium Fluoride → HCID 86641264, compound

Participants

Reaction Steps

1.40 g (2.64 mmol) of [2-isopropoxy-5-(2-trimethylsilanyl-ethanesulfonyl)-phenyl]-[5-(tetrahydro-pyran-4-yl)-1,3-dihydro-isoindol-2-yl]-methanone was dissolved in 14 ml of THF and treated with 4.0 ml (4.0 mmol) of a 1 M solution of TBAF in THF at 60° C. during 3.5 hours. The reaction mixture was poured on an aqueous solution of citric acid/NaCl, then extracted with MTBE/THF 1:1. The organic solvent was evaporated, the residue was dissolved in MeOH/water (3:1) and treated with 600 mg of NaHCO3. After evaporation, the residue was purified chromatographically on a reverse phase column (RP-18, water/methanol) to provide 0.66 g (55%) of the title compound as a white foam. MS (m/e): 430.2 [M+H]+.

Provenance & Evidence