Sodium Fluoride → HCID 59199358, compound

Participants

Reaction Steps

To a solution of 3-(3,3-dimethyl-indan-1-yl)-3H-imidazole-4-carboxylic acid methyl ester (1.31 g, 4.85 mmol), which can be prepared as described in Example 2, in THF (405 mL) at 0° C. is added LiAlH4 (220 mg, 5.6 mmol). The reaction is permitted to stir at room temperature for 2 hours at which time the reaction is cooled to 0° C., charged with sodium fluoride (205 mg, 4.88 mmol), and diluted with water. The reaction is brought to room temperature and stirred overnight. The reaction is then filtered and the eluent is extracted three times with ethyl acetate. The combined organic extracts are dried with Na2SO4, filtered and concentrated. The resulting residue is purified by silica gel flash chromatography (methanol-dichloromethane, 0:1 to 1:10) to provide 3-(3,3-dimethyl-indan-1-yl)-3H-imidazol-4-yl]-methanol; MS: (ESI) m/z 243.1 (M+H)+.

Provenance & Evidence