[OH:1][C@H:2]1[CH2:6][CH2:5][NH:4][C@H:3]1[CH3:7].[Cl:8][C:9]1[C:16]([CH3:17])=[C:15](F)[CH:14]=[CH:13][C:10]=1[C:11]#[N:12].C(=O)([O-])[O-].[Li+].[Li+]>CS(C)=O>[Cl:8][C:9]1[C:16]([CH3:17])=[C:15]([N:4]2[CH2:5][CH2:6][C@H:2]([OH:1])[C@@H:3]2[CH3:7])[CH:14]=[CH:13][C:10]=1[C:11]#[N:12]A mixture of (2S,3S)-3-hydroxy-2-methylpyrrolidine, 2-chloro-4-fluoro-3-methylbenzonitrile (424 mg), lithium carbonate (370 mg) and DMSO (12.5 ml) was stirred at 100° C. for 2 hr. The reaction mixture was cooled and partitioned between water and ethyl acetate. The organic layer was washed with water, dried (sodium sulfate), and concentrated. The obtained residue was purified by silica gel column chromatography (ethyl acetate-hexane), and crystallized from ethyl acetate-hexane to give the title compound (114 mg) as crystals.
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