C([Li])CCC.[C:6]1([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1.CN(C)[CH:23]=[O:24]>CCCCCC.CCOCC>[N:16]1([C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:15]=2[C:14]([CH:23]=[O:24])=[CH:13][CH:12]=[CH:11]3)[CH2:20][CH2:19][CH2:18][CH2:17]1n-Butyllithium (14.7 ml of a 1.7 M solution in hexane) was added dropwise to a stirred solution of 1-(1-naphthyl)pyrrolidine (25.00 mmol, 5.00 g) in dry ether (50 ml) at −20° C. under argon. After 48 hours a solution of dry N,N-dimethylformamide (6.2 ml, 75.00 mmol) in ether (10 ml) was added dropwise at −78° C. to the reaction mixture. The mixture was allowed to warm to −20° C. over 4 hours, then quenched with a solution of methanol (15 ml) and allowed to warm to room temperature. The reaction mixture was diluted with ether (100 ml), washed with water (3×150 ml) and with brine (150 ml), dried over MgSO4 and evaporated under reduced pressure. The residue was purified by column chromatography using dichloromethane as eluent to afford the aldehyde which was crystallized from hexane.
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