Pyrrolidine → HCID 54196280, compound

Participants

Reaction Steps

To an ice-cooled solution of the product from step b in acetonitrile (25 ml) was added pyrrolidine (6.41 ml, 76.8 mmol). The coolant was removed and the reaction mixture was stirred at ambient temperature for 20 h. The mixture was partitioned between ethyl acetate (100 ml) and water (100 ml). The aqueous phase was discarded and the organic phase extracted with aqueous 2M hydrochloric acid (100 ml). The organic phase was discarded and the aqueous phase was washed with further ethyl acetate (50 ml). The pH of the aqueous phase was adjusted to pH 11 and then extracted twice with chloroform (100 ml). The combined organic phases were washed with brine (100 ml) and dried over anhydrous magnesium sulfate. The filtrate was evaporated at reduced pressure to afford the title compound (4.34 g, 100%). 1H NMR 5.54 (1H, br s), 3.26-3.20 (2H, m), 2.50-2.40 (6H, m), 2.05 (3H, s), 1.85-1.73 (14H, m), 1.52-1.50 (4H, m), 1.36-1.33 (4H, m).

Provenance & Evidence