O1CCCC1.C([O:8][C:9](=O)[C@H:10]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:11][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)=O)C.O>C(OCC)(=O)C>[C:26]([O:25][C:23]([N:22]1[C@@H:10]([CH2:9][OH:8])[CH2:11][CH2:12][C@H:13]1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)=[O:24])([CH3:29])([CH3:28])[CH3:27]Ice-cold lithium borohydride (277 mg) was added to a tetrahydrofuran (40 mL) solution of (2R,5S)-5-(4-chlorophenyl)pyrrolidine-1,2-dicarboxylic acid 1-t-butyl ester 2-ethyl ester (3 g) obtained in Example 8. Stirring was continued for 30 minutes at the same temperature and for 13 hours at room temperature. Water and ethyl acetate were added, and the organic layer was partitioned. The organic layer was washed with brine and was dried over anhydrous magnesium sulfate. The solvent was removed under a vacuum, and the title compound (2.64 g) was obtained. The physical property values are as follows.
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