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

HRID 340486
Notes
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Reaction equation

HRID 340486 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 21901440N,N-dimethylformamide methanolHCID 231118872-Oxa-6-azaspiro[3.3]heptane

Product 1

HCID 686220756-(5-Nitropyridin-2-yl)-2-oxa-6-azaspiro[3.3]heptaneYield 54.9%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

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

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

Sources & evidence

ORD record
ord-8e1d96e161e34dd9939da2f02031ad46
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08895585B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes