Hydrochloric Acid → HCID 86729548, compound

Temperature

60 °C

To a solution of 1-(thiophen-2-yl)cyclopropanecarbonitrile (14.9 g) in tetrahydrofuran (100 mL) was added 1.1M borane.tetrahydrofuran complex (100 mL) at room temperature, and the mixture was stirred at 60° C. overnight. 6M Aqueous hydrochloric acid solution (20 mL) was carefully added to the reaction mixture, and the mixture was stirred at 60° C. for 0.5 hr. The reaction mixture was allowed to cool to room temperature, and tetrahydrofuran was evaporated under reduced pressure. The obtained residue was diluted with water, and washed with ethyl acetate. The aqueous layer was basified with 8M aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was dissolved in ethyl acetate, 4M hydrochloric acid/ethyl acetate solution (30 mL) was added, and the solvent was evaporated under reduced pressure. The obtained solid was recrystallized from ethanol-ethyl acetate to give the title compound (10.5 g) as white needle crystals.

1. stirringthe mixture was stirred at 60° C. for 0.5 hr
2. temperatureto cool to room temperature
3. customtetrahydrofuran was evaporated under reduced pressure
4. additionThe obtained residue was diluted with water
5. washwashed with ethyl acetate
6. extractionthe mixture was extracted with ethyl acetate
7. dry with materialThe extract was dried over anhydrous magnesium sulfate
8. customthe solvent was evaporated under reduced pressure
9. dissolutionThe obtained residue was dissolved in ethyl acetate
10. addition4M hydrochloric acid/ethyl acetate solution (30 mL) was added
11. customthe solvent was evaporated under reduced pressure
12. customThe obtained solid was recrystallized from ethanol-ethyl acetate

ORD record

ord-cc521573067a43ccbf09cb6eb818d383

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722660B2