Potassium Carbonate → 6-(5-Nitropyridin-2-yl)-2-oxa-6-azaspiro[3.3]heptane

HRID 2406741Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH2:7]1[C:10]2([CH2:13][NH:12][CH2:11]2)[CH2:9][O:8]1.CO.CN(C=O)C.Cl[C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][N:23]=1>O>[N+:28]([C:25]1[CH:26]=[CH:27][C:22]([N:12]2[CH2:13][C:10]3([CH2:9][O:8][CH2:7]3)[CH2:11]2)=[N:23][CH:24]=1)([O-:30])=[O:29]

Participants

Conditions

Temperature: 80 °C

Procedure

Potassium carbonate (78 mg) and 2-oxa-6-azaspiro[3.3]heptane (30 mg) were added to a methanol/DMF (1 ml/2 ml) solution containing 2-chloro-5-nitropyridine (30 mg), followed by stirring at 80° C. for 3 hours. The reaction solution was adjusted to room temperature, and water was added, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:1 to 1:4), and a white solid of 6-(5-nitropyridin-2-yl)-2-oxa-6-azaspiro[3.3]heptane (23 mg) was thus obtained.

Workup

customwas adjusted to room temperature
extractionfollowed by extraction with ethyl acetate
washThe resultant was washed with saturated saline
dry with materialdried over anhydrous sodium sulfate
distillationthe solvent was distilled away under reduced pressure
customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:1 to 1:4)

Sources & evidence

ORD record: ord-c6d80842c92140b588af652b8bd3ed68
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809371B2

Reaction notes

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