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Step F Synthesis of 5-(trifluoromethyl)indan-1-ol: To a solution of 5-(trifluoromethyl)indan-1-one (0.7 g, 3 mmol) in THF (5 mL) was slowly added sodium borohydride (0.1 g, 3 mmol), followed by the dropwise addition of MeOH (1 mL), under the cooling conditions in an ice bath. The reaction mixture was stirred at room temperature for 30 min before the reaction was quenched with saturated aqueous NaHCO3 solution. The reaction solution was extracted with EtOAc (2×) and the combined organic phases were washed with saturated brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with 20% EtOAc/hexane as eluent to afford the target compound 5-(trifluoromethyl)indan-1-ol (0.65 g, 92%) as a colorless oil.LC/MS analysis: calculated value of C10H9F3O (M+H)+ 203; measured value 185.1 (M+H-H2O)+.

[1] Patent: US2005/261310, 2005, A1. Location in patent: Page/Page column 25
[2] ACS Medicinal Chemistry Letters, 2010, vol. 1, # 9, p. 483 - 487
[3] Angewandte Chemie - International Edition, 2011, vol. 50, # 7, p. 1702 - 1706