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

To the solution of 1-tert-butoxycarbonyl-4-hydroxypiperidine (20.13 g, 10 mmol) and triethylamine (16.7 mL, 120 mmol) in THF (200 mL) was added dropwise methanesulfonyl chloride (9.3 mL, 120 mmol) under ice cooling, and the mixture was stirred at the same temperature for 3 hours. To the mixture was added water (200 mL), and the mixture was extracted with ethyl acetate (200 mL, 100 mL×2). The organic layer was washed with 1N-hydrochloric acid (50 mL×2), a saturated aqueous solution of sodium hydrogencarbonate (50 mL×2), saturated sodium chloride solution (50 mL), successively, dried over magnesium sulfate and concentrated under reduced pressure. To the concentrate were added diisopropyl ether (100 ml) and hexane (100 mL), and the resulting precipitates were collected by filtration. The precipitates were washed with diisopropyl ether/hexane (1/1) mixed solvent (100 mL), and dried under reduced pressure to give the titled compound (25.65 g, 92 mmol, Yield 92%) as white crystals.

1. extractionthe mixture was extracted with ethyl acetate (200 mL, 100 mL×2)
2. washThe organic layer was washed with 1N-hydrochloric acid (50 mL×2)
3. dry with materiala saturated aqueous solution of sodium hydrogencarbonate (50 mL×2), saturated sodium chloride solution (50 mL), successively, dried over magnesium sulfate
4. concentrationconcentrated under reduced pressure
5. additionTo the concentrate were added diisopropyl ether (100 ml) and hexane (100 mL)
6. customthe resulting precipitates
7. filtrationwere collected by filtration
8. washThe precipitates were washed with diisopropyl ether/hexane (1/1)
9. additionmixed solvent (100 mL)
10. customdried under reduced pressure

ORDレコード

ord-0ecd3a62356b4da2b810c6c82f785d5d

出典データセット

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07348324B2