Trifluoroacetic acid → 4-(5-Chloro-isoquinolin-6-yloxy)-cyclohexanone

Participants

Reaction Steps

549 mg (1.72 mmol) 5-Chloro-6-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-isoquinoline (78) were dissolved in 20 ml THF/H2O (3:1). 1 ml TFA was added and the mixture was stirred at room temperature. After 1 h, 2 ml TFA were added and the temperature was increased to 50° C. After 5 d at 50° C., 2 ml TFA were added. After one additional day, 2 ml TFA were added and the temperature was increased to 100° C. After 5 h, the reaction was allowed to cool down to room temperature and the mixture was diluted with dichloromethane and H2O, Solid NaHCO3 was added for neutralization. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic layers were dried over MgSO4 and evaporated. After final purification by preparative HPLC, 533 mg of the title compound as trifluoroacetate were obtained. Rt=0.88 min (Method #4). Detected mass: 276.2/278.2 (M+H+).

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