Hydrochloric Acid → 1,2,6,7-tetrahydro-8H-cyclopenta[b]furo[3,2-d]pyridin-8-one

HRID 2389914Notes

Reaction equation

[H-].[Na+].COC(=O)[CH2:6][CH2:7][C:8]1[N:13]=[CH:12][C:11]2[O:14][CH2:15][CH2:16][C:10]=2[C:9]=1[C:17]([O:19]C)=O.Cl>O1CCCC1.CO>[CH2:16]1[C:10]2=[C:9]3[C:17](=[O:19])[CH2:6][CH2:7][C:8]3=[N:13][CH:12]=[C:11]2[O:14][CH2:15]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 65% sodium hydride (1.38 g, 37.4 mmol) in tetrahydrofuran (10 mL) were added a solution of methyl 5-(3-methoxy-3-oxopropyl)-2,3-dihydrofuro[2,3-c]pyridine-4-carboxylate (1.98 g, 7.46 mmol) in tetrahydrofuran (80 mL) and methanol (0.2 mL), and the mixture was stirred at 80° C. for 10 min. 12M Hydrochloric acid (40 mL) was added thereto under ice-cooling, and the organic solvent was evaporated under reduced pressure. The residual aqueous solution was stirred at 150° C. for 20 min, the reaction mixture was basified with 8M aqueous sodium hydroxide solution under ice-cooling, and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60) to give the title compound (886 mg, yield 68%).

Workup

temperatureunder ice-cooling
customthe organic solvent was evaporated under reduced pressure
stirringThe residual aqueous solution was stirred at 150° C. for 20 min
temperaturecooling
extractionextracted with ethyl acetate
dry with materialThe extract was dried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60)

Sources & evidence

ORD record: ord-6b6a489d32bf48bebe6f7cf64a12a6c3
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273761B2

Reaction notes

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