Triethylamine → (+/-)-(1,3,4,9-Tetrahydro-beta-carboline-2-yl)-(5-nitro-2,4,6,7-tetramethyldihydrobenzofuran-2-yl)methanone

HRID 1987771ノート

反応式

HRID 1987771 の反応式
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][NH:2]1.C(N(CC)CC)C.[CH3:21][C:22]1([C:37](Cl)=[O:38])[CH2:26][C:25]2[C:27]([CH3:36])=[C:28]([N+:33]([O-:35])=[O:34])[C:29]([CH3:32])=[C:30]([CH3:31])[C:24]=2[O:23]1>CN(C=O)C>[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][N:2]1[C:37]([C:22]1([CH3:21])[CH2:26][CH:25]2[CH:27]([CH3:36])[C:28]([N+:33]([O-:35])=[O:34])=[C:29]([CH3:32])[C:30]([CH3:31])=[C:24]2[O:23]1)=[O:38]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 107838Tetrahydro-beta-carbolineHCID 231183052,4,6,7-Tetramethyl-5-nitro-2,3-dihydro-1-benzofuran-2-carbonyl chloride

生成物 1

HCID 68846049(+/-)-(1,3,4,9-Tetrahydro-beta-carboline-2-yl)-(5-nitro-2,4,6,7-tetramethyldihydrobenzofuran-2-yl)methanone

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

0.5 g of 2,4,6,7-tetramethyl-5-nitrodihydrobenzofuran-2-carboxylic acid, 20 ml of methylene chloride and 0.27 g of thionyl chloride were added, followed by heating at reflux for 2 hours. After returning the temperature to room temperature, the solvent was distilled off to obtain 2,4,6,7-tetramethyl-5-nitro-2,3-dihydrobenzofuran-2-carbonyl chloride. To 0.33 g of 2,3,4,9-tetrahydro-1H-beta-carboline, 0.23 g of triethylamine and 15 ml of DMF, a solution prepared by dissolving 2,4,6,7-tetramethyl-5-nitro-2,3-dihydrobenzofuran-2-carbonyl chloride in DMF was added, followed by stirring overnight at room temperature. The mixture was poured into ice-water and a crystal was collected by filtration. The crystal was dissolved in chloroform, washed with saturated saline and dried over anhydrous magnesium sulfate and, after the solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (chloroform:methanol=100:1) to obtain 0.54 g of the objective product.

後処理

  1. additionwas added
  2. filtrationa crystal was collected by filtration
  3. dissolutionThe crystal was dissolved in chloroform
  4. washwashed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationafter the solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (chloroform:methanol=100:1)

出典と根拠

ORDレコード
ord-1e0e59e9c8bd42c79d5d45804f5f71f9
出典データセット
uspto-grants-2009_06
特許番号
US07553837B2

反応ノート

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