Methanol → (4s)-5-(4-Fluorophenyl)-7-isopropyl-2,2-dimethyl-6-[4-(trifluoromethoxy)benzyl]chroman-4-ol

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Reaction Steps

230 μl (1.29 mmol) of borane/N,N-diethylaniline complex are added slowly to a solution of 7.23 mg (50 μmol) of (1R,2S)-1-aminoindan-2-ol in 8 ml of tetrahydrofuran, and the mixture is stirred for 30 min. A solution of 163 mg (320 μmol) of rac-5-(4-fluorophenyl)-6-{fluoro[4-(trifluoromethoxy)phenyl]methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one (Example 25A) in 8 ml of tetrahydrofuran is then slowly added dropwise. The mixture is stirred at room temperature overnight, methanol is then added and the solvent is removed under reduced pressure. The residue is taken up in ethyl acetate and washed in each case twice with 1 M hydrochloric acid and saturated sodium bicarbonate solution and once with saturated sodium chloride solution. The organic phase is dried over sodium sulfate and concentrated under reduced pressure. Purification of the residue by preparative HPLC (method 1) gives the target product.

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