Methanesulfonyl chloride → (S)-2-Benzyl-4-(3-cyclopentyloxy4-methoxy-phenyl)-1-methanesulfonyl-piperazine

関与物質

反応手順

A solution of the bis-hydrochloride salt of (S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine (50 mg, 0.11 mmol) in pyridine (1 mL) was treated with methanesulfonyl chloride (26 μL, 0.34 mmol) and stirred at room temperature for 16 h. The reaction mixture was evaporated and partitioned between EtOAc (2 mL) and a saturated aqueous NaHCO3 solution (2 mL). The organic component was separated, dried over MgSO4, filtered, and evaporated to an oil which was purified by silica gel flash chromatography with 30% then 40% EtOAc/hexane as eluant to afford the title compound as an oil (46 mg, 91%). 1H NMR (CDCl3) 7.36-7.23 (m, 5H), 6.78 (d, J=8.6, 1H), 6.48 (br s, 1H), 6.42 (br d, J=8.1, 1H), 4.71 (m, 1H), 4.30 (br t, 1H), 3.80 (s, 3H), 3.77 (m, 1H), 3.56-3.19 (m, 5H), 2.80-2.76 (m, 2H), 2.55 (s, 3H), 2.04-1.90 (m, 2H), 1.87-1.84 (m, 4H), 1.62-1.60 (m, 2H). LC/MS (Method A) 7.25 min, [M+1]+ 445.

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