Toluene → HCID 57495614, compound

Participants

Reaction Conditions

Reaction Steps

In this case, treatment of (3-adamantan-2-yl-1-isopropyl-ureido)-phenyl-acetic acid methyl ester with diisobutylaluminium hydride as described in example 1, step B] did not result in the formation of the desired material. Alternatively, (3-adamantan-2-yl-1-isopropyl-ureido)-phenyl-acetic acid methyl ester (200 mg) was dissolved in DCM (3 mL) and toluene (3 mL) under argon and treated with sodium dihydrido-bis-(2-methoxyethoxy)-aluminate (Red-Al™, 3.5 M in toluene, 0.09 mL) at −78° C. After addition of the reducing agent, the mixture was stirred at −78° C. for 30 minutes and was then allowed to warm to 0° C. The reaction mixture was quenched with 1M potassium sodium tartrate solution (10 mL) and then poured into 25% HCl (25 mL) containing a small amount of ice. The aqueous mixture was saturated with NaCl and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over Na2SO4, and evaporated to give a crude product. This material was subjected to flash chromatography using a gradient of 10 to 40% ethyl acetate in heptane followed by a second flash chromatography using DCM and by DCM/CH3CN 9:1 as eluents. This procedure provided 3-adamantan-2-yl-1-isopropyl-5-phenyl-imidazolidine-2,4-dione (116 mg) as the major product whereas the desired material 1-adamantan-2-yl-3-isopropyl-4-phenyl-1,3-dihydro-imidazol-2-one was obtained as the minor component (colorless oil, 14 mg). MS (EI): 336.2 (M+).

Provenance & Evidence