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

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.

1. extractionextracted with dichloromethane (50 mL×3)
2. washThe combined organic phase was washed with saturated sodium chloride solution (50 mL×3)
3. dry with materialdried over anhydrous magnesium sulfate
4. filtrationfiltered
5. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-3f79f3769c0144378475a68468bb997a

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691822B2