C(N(CC)CC)C.Cl.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:20][CH2:19][NH:18][CH2:17]2)=[CH:12][CH:11]=1.Cl[C:22]([O:24][CH3:25])=[O:23]>C1COCC1.O>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]2[CH2:20][CH2:19][N:18]([C:22]([O:24][CH3:25])=[O:23])[CH2:17]2)=[CH:14][CH:15]=1Triethylamine (192 mg, 1.9 mmol) was added to a suspension of 3-(4-bromophenyl)pyrrolidine hydrochloride (200 mg, 0.76 mmol) in anhydrous THF (5 mL). The reaction mixture was stirred for 5 minutes and treated with methyl chloroformate (0.1 g, 1.05 mmol). The reaction mixture was stirred for 16 hours at room temperature. The reaction mixture was diluted with water and extracted with EtOAc (2×15 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to give methyl 3-(4-bromophenyl)pyrrolidine-1-carboxylate (0.24 g, quantitative yield) as an oil which was used for next step directly. MS (ES+) 283.9 (M+H)+.
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