Hydrochloric Acid → 2-Cyclopentyl-2-(3,3,3-trifluoropropylsulfonyl)acetonitrile

Temperature

0 °C

A mixture of 1.00 g of (3,3,3-trifluoropropylsulfonyl)acetonitrile, 30 ml of tetrahydrofuran, 0.12 g of DL-proline and 1.01 g of cyclopentanone was heated and stirred for 6 hours under the reflux condition. The reaction mixture was cooled to 0° C., and 0.42 g of sodium borohydride was added thereto. The mixture was stirred at room temperature for 6 hours. After the reaction mixture was cooled to 0° C., 10 ml of water and 30 ml of ethyl acetate were added. While the mixture was stirred, 50 ml of 1N hydrochloric acid was added dropwise thereto, followed by extraction with 30 ml of ethyl acetate twice. Organic layers were combined, washed successively with 30 ml of an aqueous saturated sodium hydrogen carbonate solution and 30 ml of an aqueous saturated sodium chloride solution, dried over sodium sulfate, filtered, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.01 g of 2-cyclopentyl-2-(3,3,3-trifluoropropylsulfonyl)acetonitrile (referred to as the present compound (46)) represented by the following formula (46).

1. temperaturewas heated
2. stirringThe mixture was stirred at room temperature for 6 hours
3. temperatureAfter the reaction mixture was cooled to 0° C.
4. stirringWhile the mixture was stirred
5. extractionfollowed by extraction with 30 ml of ethyl acetate twice
6. washwashed successively with 30 ml of an aqueous saturated sodium hydrogen carbonate solution and 30 ml of an aqueous saturated sodium chloride solution
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure

ORD record

ord-3344b49c4b9349cc9b38f0922ae1e108

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08247596B2