Nitric Acid → 5'-Nitrospiro[1-azabicyclo [2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine]

HRID 1786260Notes

Reaction equation

HRID 1786260 reaction equation
[O:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH2:3][C:2]21[CH:14]1[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]1)[CH2:10]2.[N+:17]([O-])([OH:19])=[O:18].C(=O)([O-])[O-].[Na+].[Na+]>S(=O)(=O)(O)O>[N+:17]([C:8]1[CH:9]=[C:4]2[CH2:3][C:2]3([CH:14]4[CH2:13][CH2:12][N:11]([CH2:16][CH2:15]4)[CH2:10]3)[O:1][C:5]2=[N:6][CH:7]=1)([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 9815800Spiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine]

Product 1

HCID 104004255'-Nitrospiro[1-azabicyclo [2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine]Yield 51%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A mixture of spiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (325 mg, 1.5 mmol) and fuming nitric acid (0.27 mL, 5.74 mmol) in sulfuric acid (0.75 mL) was heated at 70° C. to 80° C. for 24 hours. The resulting viscous solution was poured onto 15 g of ice and basified to pH>10 with solid sodium carbonate. The resulting mixture was extracted with chloroform (4×15 mL), dried (MgSO4), filtered, and evaporated under reduced pressure. Purification by flash chromatography through silica gel, eluting with ammoniated chloroform/methanol (95:5), provided the title compound (200 mg, 0.765 mmol, 51%) as a light yellow solid: electrospray MS 262 ([MH]+, 100).

Workup

  1. temperaturewas heated at 70° C. to 80° C. for 24 hours
  2. extractionThe resulting mixture was extracted with chloroform (4×15 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customPurification by flash chromatography through silica gel
  7. washeluting with ammoniated chloroform/methanol (95:5)

Sources & evidence

ORD record
ord-e2bcaeee572442e29ef44100865b22cc
Source dataset
uspto-grants-2009_03
Patent number
US07507744B2

Reaction notes

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