C(OC([N:11]1[CH2:15][C@H:14]([CH:16]=[CH2:17])[C@H:13]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:12]1)=O)C1C=CC=CC=1.[Na].N>O1CCCC1>[C:22]([O:21][C:19]([NH:18][C@H:13]1[C@@H:14]([CH:16]=[CH2:17])[CH2:15][NH:11][CH2:12]1)=[O:20])([CH3:25])([CH3:24])[CH3:23]A solution of (3S,4S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-vinylpyrrolidine (275 mg, 0.794 mmol) in tetrahydrofuran (5 mL) and sodium (300 mg, 13.0 mmol) were sequentially added to liquid ammonia (80 mL) at −78° C., and the mixture was stirred at the same temperature for 0.5 hours. The solvent was removed, followed by dilution with chloroform (80 mL). The resultant mixture was washed sequentially by 1 mol/L sodium hydroxide (30 mL) and saturated brine (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure, to thereby yield the title compound as a colorless oily substance (168 mg, 100%).
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