Water → rac-(4aR,7aS)-octahydrospiro[cyclopenta[c]pyridine-6,2'-[1,3]dioxolane]

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Reaction Steps

In 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.

Provenance & Evidence