Pyridine → HCID 131731333, compound

Temperature

100 °C

A mixture of (rac)-3-benzyl-6-oxa-3-aza-bicyclo[3.2.1]octan-8-one (500 mg, 2.30 mmol), hydroxylamine hydrochloride (224 mg, 3.22 mmol) and pyridine (0.32 mL) in ethanol (5 mL) was heated to 100° C. for 2 hours. The reaction mixture was concentrated under reduced pressure. 2.5 N Aqueous sodium hydroxide solution (10 mL) was added to the residue. The resulting solution was extracted with ethyl acetate (50 mL), washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel with 5-10% ethyl acetate/hexane mixture as eluent to afford the title compound as a brown sticky liquid (220 mg, 43%).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. addition2.5 N Aqueous sodium hydroxide solution (10 mL) was added to the residue
3. extractionThe resulting solution was extracted with ethyl acetate (50 mL)
4. washwashed with water and brine
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe crude product was purified by column chromatography on silica gel with 5-10% ethyl acetate/hexane mixture as eluent

ORD record

ord-88ba52d19a1a48d0841cf7ad701bc1eb

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703763B2