Water → HCID 86664653, compound

Water (35 mL) and sodium azide (15.1 g, 232 mmol) were added to a solution of the crude (5,6-dihydro-4H-pyran-2-yl)methyl methanesulfonate (about 193 mmol) in N,N-dimethylformamide (350 mL), and the mixture was stirred at room temperature for 20 hours. Water (300 mL) was added to the reaction solution, followed by extraction with ethyl acetate (1.5 L). The resulting organic layer was washed with water (3×200 mL) and brine (200 mL). The organic layer was dried over anhydrous sodium sulfate and then filtered, and the solvent was evaporated under reduced pressure to about 300 mL. The resulting crude title compound solution was used for the next reaction without purification.

1. extractionfollowed by extraction with ethyl acetate (1.5 L)
2. washThe resulting organic layer was washed with water (3×200 mL) and brine (200 mL)
3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
4. filtrationfiltered
5. customthe solvent was evaporated under reduced pressure to about 300 mL
6. customThe resulting crude title compound solution was used for the next reaction without purification

ORD record

ord-298f26ac1d2e49d5859f21ca16c3d012

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08618094B2