Nitromethane → Methyl 1-benzyl-5-(nitromethylene)-2-pyrrolidinecarboxylate

HRID 253168Notes

Reaction equation

HRID 253168 reaction equation
F[B-](F)(F)F.[CH2:6]([N+:13]1[CH:14]([C:21]([O:23][CH3:24])=[O:22])[CH2:15][CH2:16][C:17]=1OCC)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CCN(CC)CC.[CH3:32][N+:33]([O-:35])=[O:34]>C(Cl)Cl>[CH3:24][O:23][C:21]([CH:14]1[CH2:15][CH2:16][C:17](=[CH:32][N+:33]([O-:35])=[O:34])[N:13]1[CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:22]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 8471TriethylamineHCID 871773091-Benzyl-5-ethoxy-2-methoxycarbonyl-3,4-dihydro-2h-pyrrolium tetrafluoroborate

Product 1

HCID 66846370Methyl 1-benzyl-5-(nitromethylene)-2-pyrrolidinecarboxylateYield 18.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the mixture obtained in Example 1C (0.2 mol) in 130 mL CH2Cl2 at ambient temperature was added Et3N (33.5 mL, 0.24 mol) followed by CH3NO2 (13 mL, 0.24 mol). The mixture stirred at ambient temperature for 8 h then was diluted with CH2Cl2, the layers were separated and the organic layer was washed with 20 mL 5% H2SO4 and 20 mL brine. The organic layer was dried over anhydrous Na2SO4, concentrated and purified via column chromatography (SiO2, 50% hexanes-EtOAc) to give 10.2 g of the title compound (36.9 mmol). MS (DCl/NH3) m/z 277 (M+H)+.

Workup

  1. customthe layers were separated
  2. washthe organic layer was washed with 20 mL 5% H2SO4 and 20 mL brine
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. custompurified via column chromatography (SiO2, 50% hexanes-EtOAc)

Sources & evidence

ORD record
ord-aabf2505b7e144e2b4f34fde01440cc3
Source dataset
uspto-grants-2011_01
Patent number
US07872010B2

Reaction notes

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