Formic Acid → (S)-4-bromo-5-trifluoromethyl-indan-1-ol

Participants

Reaction Steps

Under argon atmosphere: 1.89 ml (13.6 mmol) TEA are dissolved in 15.0 ml DCM. Under ice cooling 0.59 ml (15.8 mmol) of formic acid are added. At r.t. 100 mg (3.58 mmol) of 4-bromo-5-trifluoromethyl-indan-1-one and 49.6 mg (0.07 mmol) of chloro{[(1S,2S)-(−)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido}-(mesitylene)-ruthenium(II) are added. The reaction mixture is stirred at r.t. for 48 h. The mixture is diluted with 20 ml 1N aq. HCl. The phases are separated. The aq. phase is washed with DCM. The combined organic layers are washed with brine, dried and the solvent is evaporated. The residue is chromatographed on silica gel (CH/EtOAc=75/25→50/50) to give the title compound. Yield: 1.03 g; LC (method 1): tR=1.01 min.

Provenance & Evidence