Trimethylamine oxide → HCID 22645390, compound

Temperature

0 °C

To a stirred solution of 1-hexanoyl-3,4-dimethyl-4-(3-vinylphenyl)-piperidine (Preparation 8, 50 mg, 0.16 mmol) in bis(2-methoxyethyl)ether (1.5 mL) at 0° C. under nitrogen was added dropwise borane (1.0 M in tetrahydrofuran, 0.35 mL, 0.35 mmol). The reaction mixture was stirred at 0° C. for 30 minutes and then for 2 hours at room temperature. Trimethylamine N-oxide (48 mg, 0.64 mmol) was subsequently added and the reaction mixture heated at reflux under a nitrogen atmosphere for 2 hours. To the cooled reaction was then added diethyl ether (10 mL) and saturated aqueous sodium chloride solution (10 mL). The phases were separated and the aqueous layer was further extracted with diethyl ether (10 mL). The combined organics were dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography on silica gel (1.5 g) eluted with ethyl acetate:hexane (50:50) to give the title compound as an oil (30 mg).

1. waitfor 2 hours at room temperature
2. temperaturethe reaction mixture heated
3. temperatureat reflux under a nitrogen atmosphere for 2 hours
4. customTo the cooled reaction
5. customThe phases were separated
6. extractionthe aqueous layer was further extracted with diethyl ether (10 mL)
7. dry with materialThe combined organics were dried (MgSO4)
8. concentrationconcentrated in vacuo
9. customThe residue was purified by column chromatography on silica gel (1.5 g)
10. washeluted with ethyl acetate:hexane (50:50)

ORD record

ord-07fcec134fa6407cbb18f2998b4ced17

Source dataset

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06812236B2