4-Toluenesulfonyl chloride → 1-(tert-Butoxycarbonyl)-4-(p-toluenesulfonyloxy)piperidine

Tert-butyl 4-hydroxypiperidine-1-carboxylate (2.22 g, 10.0 mmol) was dissolved in acetonitrile (40 ml), to which triethylamine (2.74 ml, 19.7 mmol) and N,N,N′,N′-tetramethyl-1,6-diaminohexane (0.57 ml, 2.64 mmol) were added, and the mixture was cooled in an ice-bath. p-Toluenesulfonyl chloride (2.75 g, 14.4 mmol) was added to this mixture, which was allowed to return to room temperature and stirred overnight. Water was poured into the reaction mixture, and the mixture was extracted with diethyl ether. The extract was washed with brine, dried over magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1) to afford tert-butyl 4-(toluene-4-sulfonyloxy)piperidine-1-carboxylate (4.16 g, yield 89%) as a pale yellow powder.

1. additionwere added
2. temperaturethe mixture was cooled in an ice-bath
3. customto return to room temperature
4. extractionthe mixture was extracted with diethyl ether
5. washThe extract was washed with brine
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationThe filtrate was concentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1)

ORD-Eintrag

ord-beb8af66e5a848a6bc3a2c86a25f5c8a

Quelldatensatz

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07262212B2