Dimethylformamide → HCID 71227178, compound

HRID 2409879Notes

Reaction equation

HRID 2409879 reaction equation
[CH:1]12[CH2:8][CH:4]([CH2:5][CH:6]1[OH:7])[CH2:3][NH:2]2.F[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>CCOC(C)=O>[N+:16]([C:13]1[CH:14]=[CH:15][C:10]([N:2]2[CH2:3][CH:4]3[CH2:8][CH:1]2[CH:6]([OH:7])[CH2:5]3)=[CH:11][CH:12]=1)([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 21963760HCID 21963760, compound

Product 1

HCID 71227178HCID 71227178, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a round bottom flask was added 2-azabicyclo[2.2.1]heptan-6-ol (150 mg, 1.326 mmol), 1-fluoro-4-nitrobenzene (187 mg, 1.326 mmol), K2CO3 (366 mg, 2.65 mmol) and DMF (5 mL). The reaction was stirred at 65° C. for 4 hrs. The reaction was then diluted with EtOAc (35 ml). The organic solution was washed with water (3×20 ml) and saturated aqueous NaCl (20 ml). The organic layer was dried over MgSO4, filtered and concentrated. The resulting residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-100% EtOAc/Hex to give the product, 2-(4-nitrophenyl)-2-azabicyclo[2.2.1]heptan-6-ol (150 mg, 0.640 mmol, 49% yield), as a yellow solid. Anal. Calcd. for C12H14N2O3 m/z 234.2, found: 235.2 (M+H)+; 1H NMR (500 MHz, CDCl3) δ ppm 8.10 (d, J=9.90 Hz, 2 H), 6.49 (d, J=8.25 Hz, 2 H), 4.10 (s, 1 H), 3.99 (br. s., 1 H), 3.39 (dt, J=8.80, 2.75 Hz, 1 H), 2.78 (d, J=8.80 Hz, 1 H), 2.74 (br. s., 1 H), 1.97 (d, J=9.90 Hz, 1 H), 1.92 (ddd, J=13.61, 7.01, 2.47 Hz, 1 H), 1.78-1.71 (m, 2 H), 1.59-1.53 (m, 1 H); 13C NMR (126 MHz, CDCl3) δ ppm 151.32, 136.88, 126.54, 110.27, 71.10, 61.88, 54.11, 40.73, 35.91, 34.23.

Workup

  1. washThe organic solution was washed with water (3×20 ml) and saturated aqueous NaCl (20 ml)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue was purified
  6. washeluting with a gradient of 0-100% EtOAc/Hex

Sources & evidence

ORD record
ord-88b2f7a7298c4d30985a614bac250d74
Source dataset
uspto-grants-2014_08
Patent number
US08815909B2

Reaction notes

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