Acetic Acid → 1-[3-Fluoro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenyl]-4-(tetrahydropyran-4-ylmethyl)piperazine

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Reaction Steps

To a mixture of 1-[3-fluoro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenyl]piperazine (115 mg, 0.363 mmol) produced in Example (97d), tetrahydropyran-4-carbaldehyde (62 mg, 0.543 mmol) and tetrahydrofuran (7 mL) were added sodium triacetoxyborohydride (154 mg, 0.726 mmol) and acetic acid (0.021 mL, 0.363 mmol) in that order, followed by stirring for 1 hour and 30 minutes at room temperature. Ethyl acetate, saturated aqueous solution of sodium hydrogencarbonate and water were added to the reaction mixture and extraction was performed with ethyl acetate. The separated organic layer was washed with brine and then dried over anhydrous sodium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 108 mg of 1-[3-fluoro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenyl]-4-(tetrahydropyran-4-ylmethyl)piperazine as a colorless oil.

Provenance & Evidence