Diisopropylethylamine → (S)-1-(6-Iodo-3-methanesulfonyl-2-methyl-quinolin-4-yl)-piperidin-3-ol

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Reaction Steps

4-Chloro-6-iodo-3-methanesulfonyl-2-methyl-quinoline (compound of example D.2) (300 mg, 0.786 mmol), (S)-(+)-3-hydroxypiperidine (119 mg, 0.865 mmol) and N,N-diisopropyl ethyl amine (0.148 mL, 0.865 mmol) were heated in dry N,N-dimethylformamide (3 mL) for 0.5 h at 100° C. N,N-Dimethylformamide was evaporated at 40° C./0.1 mbar, the residue was extraced with dichloromethane and 10% Na2CO3, and then purified by chromatography on silica gel in dichloromethane/methanol 20:1. One obtained a yellow oil which was triturated with ethyl acetate, and the resulting white crystals were filtered off. One obtained 191 mg (54%) of white crystals. MS: m/z=447 (M+H).

Provenance & Evidence