Acetic Anhydride → HCID 57523008, compound

Temperature

110 °C

To a solution of azido alcohol 15 (150 mg, 0.58 mmol) in toluene (5 mL) was added triphenylphosphine (152 mg, 0.58 mmol) and the reaction mixture was refluxed for 3 h at 110° C. After removal of the solvent under reduced pressure, diethylether (1 mL) was added, and the mixture cooled with ice-bath. The precipitated triphenylphosphine oxide was removed by filtration and the filtrate evaporated. This procedure was repeated to remove any traces of triphenylphosphine oxide. The residue obtained was then dissolved in dry CH2Cl2 (20 mL) cooled at 0° C. To this solution was added Et3N (175.74 mg, 1.74 mmol), DMAP (4-Dimethylamine pyridine) (5 mg) and acetic anhydride (118.32 mg, 1.16 mmol) and the mixture stirred at 25° C. for further 45 minutes. After completion of reaction (monitored by TLC), the reaction mixture was quenched by addition of H2O (10 mL). The organic layer was separated, washed with brine, dried (Na2SO4) and subjected to column chromatographic purification with petroleum ether/ethyl acetate (7:3 v/v) to afford the cyclic acetamide aziridine 16.

1. customAfter removal of the solvent under reduced pressure, diethylether (1 mL)
2. additionwas added
3. temperaturethe mixture cooled with ice-bath
4. customThe precipitated triphenylphosphine oxide was removed by filtration
5. customthe filtrate evaporated
6. customto remove any traces of triphenylphosphine oxide
7. customThe residue obtained
8. temperaturecooled at 0° C
9. customAfter completion of reaction (monitored by TLC)
10. customthe reaction mixture was quenched by addition of H2O (10 mL)
11. customThe organic layer was separated
12. washwashed with brine
13. dry with materialdried (Na2SO4)
14. customsubjected to column chromatographic purification with petroleum ether/ethyl acetate (7:3 v/v)

ORD record

ord-2e9668d4c662414d85c249c39734ff9d

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150498B2