反应详情

To a solution of (3S,5R)-benzyl 3-(benzoyloxy)-5-(tert-butyl-dimethylsilyloxy)-piperidine-1-carboxylate (1 eq) in 30 mL of methanol was added 3.8M HCl in isopropanol (4 eq). The reaction mixture was allowed to stand at room temperature for 3 hours at which point it was concentrated under reduced pressure. The resulting residue was diluted with 120 mL of EtOAc, washed with sat. aq. sodium bicarbonate, brine, then dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (EtOAc:hexanes=1:1) to yield (3S,5R)-benzyl 3-(benzoyloxy)-5-hydroxypiperidine-1-carboxylate (95%). LC/MS (m/z): 355.9 (MH+). HPLC: Rt:3.62 min.

1. concentrationwas concentrated under reduced pressure
2. additionThe resulting residue was diluted with 120 mL of EtOAc
3. washwashed with sat. aq. sodium bicarbonate, brine
4. dry with materialdried over anhydrous MgSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe crude residue was purified by flash chromatography (EtOAc:hexanes=1:1)