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

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence