O1CCCC1.[C:6]1([CH2:12][N:13]2[CH2:18][CH2:17][CH2:16][C@@H:15]([NH2:19])[CH2:14]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[CH3:27][O:28][CH2:29][C:30](Cl)=[O:31]>O.C(Cl)Cl>[CH3:27][O:28][CH2:29][C:30]([NH:19][C@@H:15]1[CH2:16][CH2:17][CH2:18][N:13]([CH2:12][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:14]1)=[O:31]To a 50 ml anhydrous tetrahydrofuran solution of 5.00 g (26.3 mmol) of (R)-1-phenylmethyl-3-aminopiperidine (Referential example 7) in a 300 ml three-necked flask was added a 50 ml anhydrous tetrahydrofuran solution of 3.20 g (1.2 eg.) of triethylamine, and, to this reaction mixture was added dropwise a 50 ml anhydrous tetrahydrofuran solution of 2.85 g (1.0 eg.) of methoxyacetyl chloride under stirring and cooling with ice. After reacted for 5 hours at room temperature, methylene chloride and small amount of water were added to extract (20 ml×6). The organic layers were combined and dried over anhydrous sodium sulfate. Then, solvent was distilled off under reduced pressure and the residue thus obtained was purified by column chromatography (alumina, ethyl acetate:n-hexane=1:1) to obtain 6.67 g (yield 97 %) of title compound as a pale yellow oil.
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