Imidazole → 2-(2-(1-Benzothiophene-6-yl)ethoxy)-1-(3-hydroxy-1-pyrrolidinyl)-1-ethanone

Temperature

5 °C

0.74 g of 2-(2-(1-benzothiophene-6-yl)ethoxy)acetic acid was dissolved in 7.4 ml of methylene chloride. Thereafter, 1.36 ml of triethylamine and 0.22 g of imidazole were added to the obtained solution. Subsequently, the mixture was cooled to 5° C. Thereafter, 0.24 ml of thionyl chloride was added dropwise thereto, and the obtained mixture was stirred at the same above temperature for 1 hour. After the reaction mixture was cooled to −50° C., 0.45 ml of triethylamine and 0.32 ml of 3-pyrrolidinol were added thereto. The mixture was stirred at the same above temperature for 1 hour and then at a room temperature for 1 hour. Thereafter, water was added to the reaction mixture, and an organic layer was separated. The organic layer was successively washed with 1 mol/l hydrochloric acid, then with a 2 mol/l aqueous sodium hydroxide solution, and then with a saturated saline solution. The resultant was then dried over anhydrous magnesium sulfate. Subsequently, the solvent was distilled away under a reduced pressure, so as to obtain a light yellow oil product, 2-(2-(1-benzothiophene-6-yl)ethoxy)-1-(3-hydroxy-1-pyrrolidinyl)-1-ethanone.

1. temperatureAfter the reaction mixture was cooled to −50° C.
2. stirringThe mixture was stirred at the same above temperature for 1 hour
3. waitat a room temperature for 1 hour
4. customan organic layer was separated
5. washThe organic layer was successively washed with 1 mol/l hydrochloric acid
6. dry with materialThe resultant was then dried over anhydrous magnesium sulfate
7. distillationSubsequently, the solvent was distilled away under a reduced pressure

ORD record

ord-a7ac57e3092b46579dbecf06e59a5506

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07897594B2