Tetrabutylammonium Fluoride → HCID 71513570, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[[1-(tert-butoxycarbonyl)-2(S)-pyrrolidinyl]methoxy]-5-[(trimethylsilyl)ethynyl]pyridine (500 mg, 1.3 mmol) in anhydrous THF (43 mL) was added at 0° C. 1.0M tetra-n-butylammonium fluoride solution in THF (4.0 mL, 4.0 mmol). The reaction mixture was stirred at 0° C. for 2 h. The reaction was quenched by addition of saturated aqueous NH4Cl solution. The mixture was extracted with CH2Cl2, and the organic phase was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by CC on SiO2 eluting with EtOAc/hexane 1:4 to give 3-[[1-(tert-butoxycarbonyl)-2(S)-pyrrolidinyl]methoxy]-5-ethynylpyridine (470 mg, 98%).

Provenance & Evidence