Sodium borohydride → HCID 24965151, compound

Participants

Reaction Conditions

Reaction Steps

2-(3-Adamantan-2-yl-1-cyclopropyl-ureido)-3-methyl-butyric acid ethyl ester (110 mg) was dissolved in ethanol (5 mL) under argon and then sodium borohydride (92 mg) was added in one portion. The mixture was heated to 55° C. and stirred over night. TLC analysis confirmed complete consumption of the starting material. The mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate and was then vigorously shaken with 25% HCl. The organic layer was separated, washed with brine, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography: a first column was eluted with a gradient of methanol in DCM (0 to 5%) and a second column with a gradient of 0 to 10% methanol in DCM/CH3CN (85:15). 1-Adamantan-2-yl-3-cyclopropyl-4-isopropyl-1,3-dihydro-imidazol-2-one was obtained as a colorless oil (23 mg). MS (ESI): 301.4 (MH+).

Provenance & Evidence