Triethylamine → 1-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Temperature

0 °C

To a solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (5.0 g, 36 mmol) and triethyl amine (6.0 ml, 43 mmol) in 50 ml of THF at 0° C. under an atmosphere of nitrogen was added MsCl (3.4 ml, 43 mmol). The mixture was stirred at 0° C. for 3 h and quenched with aqueous sodium hydrogen carbonate (saturated, 100 mL). The mixture was extracted with ethyl acetate (3×100 mL). The combined organic fractions were washed with brine (1×100 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 40M, eluting with EtOAc/isohexane to hexanes to afford the title compound as a colorless solid (4.2 g, 42%). 1H-NMR (500 MHz, CDCl3) δ 4.90 (s, 1H), 3.70 (m, 2H), 3.30 (m, 2H), 3.05 (s, 3H), 1.95 (m, 2H), 1.82 (m, 2H), 1.45 (s, 9H).

1. customquenched with aqueous sodium hydrogen carbonate (saturated, 100 mL)
2. extractionThe mixture was extracted with ethyl acetate (3×100 mL)
3. washThe combined organic fractions were washed with brine (1×100 mL)
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. customthe solvent was evaporated under reduced pressure
7. customThe residue was purified by column chromatography on silica gel Biotage 40M
8. washeluting with EtOAc/isohexane to hexanes

ORD record

ord-b786ebd5f86742bea2deef6f8e219e0a

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354403B2