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

To a solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (14.0 g, 70.0 mmol) at 0° C. in triethylamine (9.9 g, 98 mmol) and dichloromethane (100 mL) was added dropwise methanesulfonyl chloride (11.2 g, 98.0 mmol). The reaction was brought to ambient temperature and stirred for 1 h. Then the reaction mixture was quenched with water (50 mL). The aqueous layer was separated and extracted with ethyl acetate (2×50 mL). The combined organic layer was washed with brine (50 mL), and dried over sodium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure to afford 243a, which was used in the next step without further purification (19.5 g, 100%). MS-ESI: [M-t-Bu]+ 224.1

1. customwas brought to ambient temperature
2. customThen the reaction mixture was quenched with water (50 mL)
3. customThe aqueous layer was separated
4. extractionextracted with ethyl acetate (2×50 mL)
5. washThe combined organic layer was washed with brine (50 mL)
6. dry with materialdried over sodium sulfate
7. customThe drying agent was removed by filtration
8. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-a51aea030bea4f0bae6e57a18ebf0466

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08716274B2