C(Cl)(=O)C(Cl)=O.[NH:7]1[CH:11]=[CH:10][C:9]([C:12]([OH:14])=O)=[CH:8]1.[NH:15]1[CH2:18][CH2:17][CH2:16]1>CN(C)C=O.ClCCl>[N:15]1([C:12]([C:9]2[CH:10]=[CH:11][NH:7][CH:8]=2)=[O:14])[CH2:18][CH2:17][CH2:16]1Oxalyl chloride (0.13 mL, 1.5 mmol) was added to a mixture of 1H-pyrrole-3-carboxylic acid (0.111 g, 1.00 mmol) and 1 drop of N,N-dimethylformamide in 5 mL of dichloromethane. The mixture was stirred for 15 h, then concentrated, then redissolved in 5 mL of dichloromethane and cooled to 0-5° C. Azetidine (0.21 mL, 2.5 mmol) was added, and the mixture was stirred for 1 h at 0-5° C. then absorbed onto silica gel and concentrated. Column chromatography (2->10% MeOH/CH2Cl2) afforded 0.059 g (39%) of azetidin-1-yl-(1H-pyrrol-3-yl)-methanone as an off-white solid.
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