Water → 2-Nitro-5-(oxetan-3-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

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Reaction Conditions

Reaction Steps

A mixture of 2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine 124d (238 mg, 1.40 mmol), oxetan-3-one (252 mg, 3.5 mmol), NaBH3CN (260 mg, 4.2 mmol), and zinc chloride (567 mg, 4.2 mmol) in methanol (10 mL) was stirred at 50° C. for 6 hours. The mixture was added to water and extracted with dichloromethane three times. The combined organic layer was concentrated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with 50:1 dichloromethane/methanol to afford 155a (200 mg, 64%). MS: [M+H]+ 225.3

Provenance & Evidence