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

HRID 747909ノート

反応式

HRID 747909 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-bc1bf318094d4437bbffd21cbd480411
出典データセット
uspto-grants-2008_07
特許番号
US07399765B2

反応ノート

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