[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@H:9]1[CH2:13][N:12]([CH2:14][CH3:15])[CH2:11][C@H:10]1[C:16]([O:18]C)=[O:17].C[Si](C)(C)[O-].[K+].[ClH:26]>C(OCC)C.O1CCOCC1>[ClH:26].[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@H:9]1[CH2:13][N:12]([CH2:14][CH3:15])[CH2:11][C@H:10]1[C:16]([OH:18])=[O:17]To a stirred solution of methyl (3S,4R)-4-(2,4-difluorophenyl)-1-ethylpyrrolidine-3-carboxylate, from preparation 18 (5.9 g, 22 mmol) in diethyl ether (59 mL) at room temperature under dry nitrogen was added potassium trimethylsilanolate (2.36 g, 26 mmol) in a single portion. The resulting mixture was stirred at room temperature under N2 for 3 hours. A solution of 4M hydrogen chloride in dioxane (20 mL) was then added and the resulting mixture was stirred under dry nitrogen at room temperature for 18 hours, and then concentrated in vacuo to afford the title compound as a white solid containing potassium chloride residues (7.0 g).
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