Tetrabutylammonium Fluoride → HCID 10425446, compound

Participants

Reaction Steps

A mixture of 1-benzyl-4-(2'-(4''-t-butyldimethylsilyloxyphenyl)-2'-oxoethyl)piperidine (Example 75, 1.21 g, 2.86 mmol), a solution of tetra-n-butylammonium fluoride (1.0 M in tetrahydrofuran, 5.7 mL, 5.7 mmol) and tetrahydrofuran (10 mL) were stirred at ambient temperature under a nitrogen atmosphere overnight. The reaction mixture was poured onto water and extracted three times with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was triturated with ethyl acetate and filtered. Drying in vacuo gave the title compound (238 mg): mp 197°-198° C.; 1H-NMR (CDCl3, 300 MHz): 7.8(d,2H,J=8), 7.4-6.8(m,7H), 3.5(s,2H), 3.2-3.0(br s,4H), 3.0-2.8(dd,4H,J=10,7), 2.5(s,1H), 2.1-1.2(m,4H); Anal.:Calcd for C20H23NO2 ·0.25H2O: C,76.53, H,7.55, N, 4.40; Found: C,76.63,76.54, H,7.47,7.31, N,4.23,4.26.

Provenance & Evidence