Hydrochloric Acid → 4-Butyl-4-(pyrrolidin-1-yl)cyclohexanone

Participants

Reaction Steps

Water (10.0 ml) and 37% hydrochloric acid (14.0 ml) were added to a solution of 1-(8-butyl-1,4-dioxaspiro[4,5]dec-8-yl)pyrrolidine (2.70 g, 10.1 mmol) in acetone (100 ml) and the mixture was stirred overnight at room temperature. Then 4 M sodium hydroxide solution was added slowly to the mixture until a pH of 10 was achieved. The mixture was extracted with diethyl ether (4×40 ml), the combined organic phases were dried with sodium sulfate and concentrated to small volume under vacuum. The crude product (2.6 g) was purified by flash chromatography (260 g, 30×5.6 cm) with ethyl acetate/methanol (9:1). Yield: 1.06 g (47%), brown oil.

Provenance & Evidence