Hydrochloric Acid → (1R)-N-(3,4-dichlorophenyl)-1,8,8-trimethyl-2,4-dioxobicyclo[3.2.1]octane-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

To an ice-cooled solution of (1R)-1,8,8-trimethylbicyclo[3.2.1]octane-2,4-dione (0.90 g, 5.0 mmole), triethylamine (0.50 g, 5.0 mmole) and 4-(dimethylamino)pyridine (0.61 g, 5.0 mmole) in dry dichloromethane (100 mL) was added a solution of 3,4-dichlorophenyl isocyanate (0.94 g, 10.0 mmole) in dry dichloromethane (25 mL). The resulting mixture was allowed to stir overnight under a nitrogen atmosphere, during which time it came up to room temperature, and then was heated at 30° C. for 24 hours. The reaction mixture was treated with 2N aqueous HCl and the layers separated. The acidic aqueous layer was extracted with two additional portions of dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate and concentrated on a rotary evaporator to give a yellow oil, which was purified by chromatography on silica gel (10% ethyl acetate/hexane) to yield a yellow oil, which was crystallized from 95% ethanol to yield the title compound as a beige solid (1.07 g, 58% yield), mp=89–91° C.; MS (−) ESI m/z=366 (M−H)−; [α]D25=+25.9° (c=1, EtOH).

Provenance & Evidence