Cesium carbonate → 5,6-Bis(nitrooxy)hexyl 3-(4-chlorophenyl)-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-yl carbonate

HRID 1643424Notes

Reaction equation

HRID 1643424 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]([C:11]3[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=3)[O:9][CH2:10][C:4]=2[C:3]=1[OH:18].C([O-])([O-])=O.[Cs+].[Cs+].[C:25](=O)([O:41]C1C=CC([N+]([O-])=O)=CC=1)[O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH:31]([O:37][N+:38]([O-:40])=[O:39])[CH2:32][O:33][N+:34]([O-:36])=[O:35]>CN(C=O)C.O>[C:25](=[O:41])([O:18][C:3]1[C:4]2[CH2:10][O:9][CH:8]([C:11]3[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=3)[C:5]=2[CH:6]=[N:7][C:2]=1[CH3:1])[O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH:31]([O:37][N+:38]([O-:40])=[O:39])[CH2:32][O:33][N+:34]([O-:36])=[O:35]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 54910CicletanineHCID 86638656HCID 86638656, compound

Product 1

HCID 446334875,6-Bis(nitrooxy)hexyl 3-(4-chlorophenyl)-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-yl carbonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of cicletanine (120 mg, 0.55 mmol) in DMF (10 mL) was added Cs2CO3 (373 mg, 1.15 mmol) and followed by 5,6-bis(nitrooxy)hexyl 4-nitrophenyl carbonate (210 mg, 0.54 mmol). The mixture was stirred at rt over night and diluted with H2O, extracted with CH2Cl2 and the organic layer was washed with brine, dried over MgSO4 and concentrated. The residue was purified by flash chromatography (Biotage SP1; column 25M; TLC method: n-hexane/ethyl acetate 5/5; Rf=0.35), affording product. 1H NMR (500 MHz, CDCl3) δ 8.08 (s, 1H), 7.36-7.27 (m, 4H), 6.21 (s, 1H), 5.34 (m, 1H), 5.26 (m, 1H), 5.13 (m, 1H), 4.77 (m, 1H), 4.48 (m, 1H), 4.32 (m, 2H), 2.51 (s, 3H), 1.84 (m, 4H), 1.69-1.55 (m, 2H).

Workup

  1. extractionextracted with CH2Cl2
  2. washthe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (Biotage SP1; column 25M; TLC method: n-hexane/ethyl acetate 5/5; Rf=0.35)
  6. customaffording product

Sources & evidence

ORD record
ord-9e7a42b875694846b30c85a94ca3ed25
Source dataset
uspto-grants-2012_02
Patent number
US08119806B2

Reaction notes

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