Ethyl Acetate → HCID 178468165, compound

In 20 ml of dry tetrahydrofuran was dissolved 1.3 g of trans-N-t-butoxycarbonyl-4-(1-t-butyldimethylsilyloxyethyl)cyclohexylmethylamine, and 5.25 ml of tetrabutylammonium fluoride (1.0M tetrahydrofuran solution) were added dropwise thereto with stirring under ice-cooling, and the mixture was stirred at room temperature for 55 minutes. Then, 5.0 ml of tetrabutylammonium fluoride (1.0M tetrahydrofuran solution) were added dropwise thereto and the mixture was stirred at room temperature overnight and further at 50° C. for 9 hours. To the reaction mixture were added 200 ml of ethyl acetate, and the mixture was washed successively with an aqueous citric acid solution, an aqueous sodium chloride solution, an aqueous sodium bicarbonate solution and an aqueous sodium chloride solution. The mixture was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: cyclohexane/ethyl acetate=2/1) to obtain 701 mg of the desired compound as a colorless crystalline solid. Further, 38 mg of the desired compound was obtained from the mother liquid.

1. additionwere added dropwise
2. temperaturecooling
3. stirringthe mixture was stirred at room temperature for 55 minutes
4. stirringthe mixture was stirred at room temperature overnight and further at 50° C. for 9 hours
5. washthe mixture was washed successively with an aqueous citric acid solution
6. dry with materialThe mixture was dried over anhydrous magnesium sulfate
7. distillationthe solvent was distilled off under reduced pressure
8. customThe residue was purified by silica gel column chromatography (eluting solvent: cyclohexane/ethyl acetate=2/1)

ORD record

ord-54ca3cdb65e246a59afea2883a379391

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05843973