HCID 54485489, compound → HCID 22127288, compound

A mixture of 1.3 g (2.1 mmol) of 2,2,2-trichloroethyl (3RS,4RS)-4-(4-bromo-phenyl)-3-(2,2,2-trichloro-ethoxycarbonyloxy)-piperidine-1-carboxylate 1.54 g of activated zinc in 20 ml of glacial acetic acid was stirred at room temperature for 5 hours. For the working-up, the zinc was filtered off, the residue was rinsed with glacial acetic acid and the solution was subsequently evaporated to dryness under reduced pressure. The residue was partitioned between 20 ml of saturated sodium carbonate solution and 30 ml of ethyl acetate, thereafter the separated aqueous phase was extracted twice with 30 ml of ethyl acetate each time. The combined organic phases were dried over sodium sulphate and evaporated under reduced pressure. Crystallization of the residue using a 1:2 mixture of ethyl acetate and hexane yielded 250 mg (46% of theory) of (3RS,4RS)-4-(4-bromo-phenyl)-piperidin-3-ol as a colourless solid; MS: 255, 257 (M)+. The mother liquor was purified by chromatography on silica gel using a 4:1 mixture of methylene chloride and methanol as the eluent. A further 101 mg (18% of theory) were obtained.

1. filtrationthe zinc was filtered off
2. washthe residue was rinsed with glacial acetic acid
3. customthe solution was subsequently evaporated to dryness under reduced pressure
4. customThe residue was partitioned between 20 ml of saturated sodium carbonate solution and 30 ml of ethyl acetate
5. extractionthe separated aqueous phase was extracted twice with 30 ml of ethyl acetate each time
6. dry with materialThe combined organic phases were dried over sodium sulphate
7. customevaporated under reduced pressure
8. customCrystallization of the residue
9. additiona 1:2 mixture of ethyl acetate and hexane

ORD record

ord-b686edc73a1f4b3680b0b774f06fcdb4

Source dataset

uspto-grants-2000_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06150526