Citric Acid → HCID 22413608, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-cyclohexyl-2-(4-(2-quinolylmethoxy)phenyl)propionic acid, prepared according to the procedure of K. Mohrs et al. U.S. Pat. No. 4,970,215, (1.37 g, 3.5 mmol) in THF (40 mL) at -10° C. was added triethylamine (0.5 mL, 3.6 mmol) and then dropwise a solution of ethyl chloroformate (0.36 mL, 3.6 mmol) in THF (10 mL). The reaction was stirred for 15 minutes at -10° to -5° C. and then was allowed to warm to 0° C. To the mixture was added sodium borohydride (380 mg, 10 mmol) followed by the dropwise addition of methanol (30 mL) for 30 minutes at 0° C. The resulting mixture was stirred for an additional 20 minutes and then was neutralized with 10% citric acid and extracted with ethyl acetate (100 mL). The ethyl acetate extract was washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 2:1 hexane-ethyl acetate to provide 1.14 g of 3-cyclohexyl-2-(4-(2-quinolylmethoxy)phenyl)propan-1-ol as an oil.

Provenance & Evidence