[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH:19]([CH2:20][OH:21])[CH2:18][NH:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])(O)=O.[Na+].Cl[C:28]([O:30][CH3:31])=[O:29]>C(OCC)(=O)C>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH:19]([CH2:20][OH:21])[CH2:18][N:17]([C:28]([O:30][CH3:31])=[O:29])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1To a vigorously stirring mixture of 3-(3-cyclopentoxy-4-methoxyphenyl)-4-(hydroxymethyl)pyrrolidine (328 mg, 1.13 mmol) in 4 mL of 1:1 ethyl acetate:sat aq NaHCO3 was added methyl chloroformate (138 mg, 1.47 mmol). When TLC analysis indicated a complete reaction the mixture was diluted with ethyl acetate, and the layers were separated. The organic layer was dried over K2CO3, filtered, and concentrated under reduced pressure to provide 3-(3-cyclopentoxy-4-methoxyphenyl)-4-hydroxymethyl-1-(methoxycarbonyl)pyrrolidine as a colorless viscous oil (273 mg, 69%). Anal. Calcd for C19H27NO5 ·0.5 H2O: C, 63.67; H, 7.87; N, 3.91. Found: C, 63.30; H, 7.75; N, 3.92.
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