Acetic Acid → 1-(2-Cyclobutyl-2,8-diazaspiro[4.5]decan-8-yl)-2-(1-(4-methoxy-2,6-dimethylphenylsulfonyl)-1,2,3,4-tetrahydroquinolin-7-yl)ethanone hydrochloride

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Reaction Steps

2-(1-(4-Methoxy-2,6-dimethylphenylsulfonyl)-1,2,3,4-tetrahydroquinolin-7-yl)-1-(2,8-diazaspiro[4.5]decan-8-yl)ethanone hydrochloride (from stage (ii)) (140 mg, 0.255 mmol), triethylamine (0.04 ml, 0.255 mmol) and cyclobutanone (0.02 ml, 0.255 mmol) were dissolved in 1,2-dichloroethane (5 ml), and sodium triacetoxy-borohydride (75 mg, 0.358 mmol) and glacial acetic acid (15 mg, 0.255 mmol) were added thereto. The reaction mixture was stirred for 15 h and then diluted with dichloromethane, and saturated sodium hydrogen carbonate solution (10 ml) was added thereto. After phase separation, the aqueous phase was extracted with dichloromethane (3×30 ml). The combined organic phases were washed with saturated sodium chloride solution (30 ml), dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel, ethyl acetate/dichloromethane/methanol/ammonia (25% aq.), 300:100:25:1). Finally, the hydrochloride was precipitated from ethereal solution (plus a small amount of acetone) with hydrogen chloride in ether (2 M) and the desired exemplary compound G-10 was thus obtained. Yield: 100 mg (65%). MS, Rt=3.4 min; m/z=566.1 [MH]+

Provenance & Evidence