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

HRID 1185218Notes

Reaction equation

[N+:1]([C:4]1[CH:12]=[C:7]2[CH2:8][NH:9][CH2:10][CH2:11][N:6]2[N:5]=1)([O-:3])=[O:2].[O:13]1[CH2:16][C:15](=O)[CH2:14]1.[BH3-]C#N.[Na+].O>CO.[Cl-].[Zn+2].[Cl-]>[N+:1]([C:4]1[CH:12]=[C:7]2[CH2:8][N:9]([CH:15]3[CH2:16][O:13][CH2:14]3)[CH2:10][CH2:11][N:6]2[N:5]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 50 °C

Procedure

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

Workup

extractionextracted with dichloromethane three times
concentrationThe combined organic layer was concentrated under reduced pressure
customthe residue was purified by silica-gel column chromatography
washeluting with 50:1 dichloromethane/methanol

Sources & evidence

ORD record: ord-4cc5b3b570c842eba85217bf05ef5e72
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669251B2

Reaction notes

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