[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]1[C@H:12]2[CH2:13][C:14]3([O:19][CH2:18][CH2:17][O:16]3)[CH2:15][C@H:11]2[CH2:10][C:9](=O)[NH:8]1.O.[OH-].[Na+]>O1CCCC1>[O:16]1[CH2:17][CH2:18][O:19][C:14]21[CH2:13][C@@H:12]1[CH2:7][NH:8][CH2:9][CH2:10][C@@H:11]1[CH2:15]2In an ice-water bath, lithium aluminium hydride (47 mg, 1.27 mmol) was dissolved in 10 mL of tetrahydrofuran followed by the addition of 10 mL of a solution of (cis)-spiro[1,3-dioxolane-2,6′-2,4,4a,5,7,7a-hexahydro-1H-cyclopenta[c]pyridine]-3′-one 14e (120 mg, 0.60 mmol) in tetrahydrofuran. The resulting solution was stirred for 1 hour, added with 1 μL of water, 1 μL of 15% sodium hydroxide solution in batches, extracted with dichloromethane (50 mL×3). The combined organic phase was washed with saturated sodium chloride solution (50 mL×3), then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure to obtain the crude title compound (cis)-spiro[1,2,3,4,4a,5,7,7a-octahydrocyclopenta[c]pyridine-6,2′-1,3-dioxolane] 14f (150 mg) as a yellow oil liquid, which was used in the next step without further furification.
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