3-Hydroxypiperidine → HCID 21836535, compound

A mixture of 1-(t-butoxycarbonyl)-3-methanesulphonyloxyazetidine (see International Patent Application Publication no. WO93/19059) (1.5 g, 4.78 mmol) and 3-hydroxypiperidine (1.9 g, 4 mol. equiv.) was heated at 110° C. for sixteen hours. The mixture was cooled to room temperature and partitioned between ethyl acetate (100 ml) and 5% aqueous sodium bicarbonate solution (100 ml). The layers were separated and the aqueous phase was extracted with a further portion of ethyl acetate (100 ml). The combined organic layers were dried over anhydrous magnesium sulphate. The solution was filtered, the solvent removed from the filtrate under reduced pressure and the crude product purified by column chromatography using silica gel eluting with methanol:dichloromethane (1:9, by volume) to give the title compound (1.4 g). TLC Rf=0.3 (silica, methanol:dichloromethane, 1:9, by volume).

1. custompartitioned between ethyl acetate (100 ml) and 5% aqueous sodium bicarbonate solution (100 ml)
2. customThe layers were separated
3. extractionthe aqueous phase was extracted with a further portion of ethyl acetate (100 ml)
4. dry with materialThe combined organic layers were dried over anhydrous magnesium sulphate
5. filtrationThe solution was filtered
6. customthe solvent removed from the filtrate under reduced pressure
7. customthe crude product purified by column chromatography

ORD record

ord-04f78d3cd599409ba4d4d409d5fe4832

Source dataset

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05968923