Methanol → (4s)-6-(4-Tert-butylbenzyl)-5-(4-fluorophenyl)-7-isopropyl-2,2-dimethylchroman-4-ol

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Reaction Steps

150 μl (840 μmol) of borane/N,N-diethylaniline complex are added slowly to a solution of 4.70 mg (30 μmol) of (1R,2S)-1-aminoindan-2-ol in 5 ml of tetrahydrofuran, and the mixture is stirred for 30 min. A solution of 100 mg (210 μmol) of rac-6-[(4-tert-butylphenyl)(fluoro)methyl]-5-(4-fluorophenyl)-7-isopropyl-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one (Example 28A) in 5 ml of tetrahydrofuran is then slowly added dropwise. After 3 h of stirring at room temperature, methanol is added and the solvent is reduced 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 then concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel (mobile phase: gradient cyclohexane→cyclohexane/ethyl acetate 10:1→5:1) gives the target product.

Provenance & Evidence