反应详情

A solution of cis (+/−)-benzyl 3-(tert-butoxycarbonylamino)-5-(hydroxymethyl)piperidine-1-carboxylate (1 eq.), perfluorobutanesulfonylfluoride (2 eq.), triethylamine-HF (4 eq.) and triethylamine (6 eq.) in tetrahydrofuran at a concentration of 0.16 M was stirred for 36 hours. Upon dilution with ethyl acetate (50×) the solution was washed with 1N HCl, NaHCO3(sat.) and brine, was dried over MgSO4, filtered, concentrated and purified by column chromatography (25-40% ethyl acetate/hexanes) to yield cis (+/−)-benzyl 3-(tert-butoxycarbonylamino)-5-(fluoromethyl)piperidine-1-carboxylate (45% yield). LCMS (m/z): 267.1 (MH+); LC Rt=4.23 min.

1. washUpon dilution with ethyl acetate (50×) the solution was washed with 1N HCl, NaHCO3(sat.) and brine
2. dry with materialwas dried over MgSO4
3. filtrationfiltered
4. concentrationconcentrated
5. custompurified by column chromatography (25-40% ethyl acetate/hexanes)