Nitromethane → 6-Nitromethyl-4-oxo-1,4,5,6,7,8-hexahydro-cyclohepta[b]pyrrole-3-carboxylic acid ethyl ester

HRID 982886ノート

反応式

HRID 982886 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[C:22](=[O:23])[CH:21]=[CH:20][CH2:19][CH2:18][C:8]=2[N:9](C(OC(C)(C)C)=O)[CH:10]=1)=[O:5])[CH3:2].[CH3:24][N+:25]([O-:27])=[O:26]>>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[C:22](=[O:23])[CH2:21][CH:20]([CH2:24][N+:25]([O-:27])=[O:26])[CH2:19][CH2:18][C:8]=2[NH:9][CH:10]=1)=[O:5])[CH3:2]

参加物

3

反応物 2

HCID 6375NitromethaneHCID 207622234-Oxo-7,8-dihydro-4H-cyclohepta[b]pyrrole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

生成物 1

HCID 698017626-Nitromethyl-4-oxo-1,4,5,6,7,8-hexahydro-cyclohepta[b]pyrrole-3-carboxylic acid ethyl ester収率 93%

実験手順

4-Oxo-7,8-dihydro-4H-cyclohepta[b]pyrrole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (6.81 g, 21.3 mmol) is dissolved in CH3NO2 (50 ml), Triton B (40% aqueous, 2.5 mL) is added quickly. The reaction mixture was kept at 80° C. for 8 h. The mixture is cooled and the solvent removed under reduced pressure. The residue is taken into 50 ml CH2Cl2 and 25 ml H2O. The aqueous phase is adjusted to slightly basic with 1N HCl and sat. NaHCO3, and extracted with CH2Cl2 (30 mL×4). Organic phases are combined, dried (Na2SO4), and evaporated. Flash chromatography (1:1 hexanes/EtOAc) provides the title compound (5.6 g, 93%) as white solid. 1H NMR (400 MHz, CD3OD) δ 7.21 (1H, s), 4.45 (2H, d), 4.20 (2H, q), 2.97-2.62 (5H, m), 2.04 (1H, m), 1.65 (1H, m), 1.27 (3H, t). MS (ES+) 281 (M+1) Step 2: Dimethylaminomethyl4-oxo-1,4,5,6,7,8-hexahydro-cyclohepta[b]pyrrole-3-carboxylic acid ethyl ester.

後処理

  1. additionTriton B (40% aqueous, 2.5 mL) is added quickly
  2. temperatureThe mixture is cooled
  3. customthe solvent removed under reduced pressure
  4. extractionextracted with CH2Cl2 (30 mL×4)
  5. dry with materialdried (Na2SO4)
  6. customevaporated

出典と根拠

ORDレコード
ord-a9f812c4763e4f7189850ab69a7721ea
出典データセット
uspto-grants-2005_03
特許番号
US06861529B2

反応ノート

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