Calcium Chloride → (+/-)-(5-Amino-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran-2-yl)-(1,3,4,9-tetrahydro-beta-carboline-2-yl)-methanone

HRID 1987772ノート

反応式

HRID 1987772 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][N:2]1[C:14]([C:16]1([CH3:31])[CH2:20][CH:19]2[CH:21]([CH3:30])[C:22]([N+:27]([O-])=O)=[C:23]([CH3:26])[C:24]([CH3:25])=[C:18]2[O:17]1)=[O:15].[Cl-].[Ca+2].[Cl-]>[Zn].C(O)C>[NH2:27][C:22]1[C:23]([CH3:26])=[C:24]([CH3:25])[C:18]2[O:17][C:16]([C:14]([N:2]3[CH2:3][CH2:4][C:5]4[C:6]5[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=5)[NH:12][C:13]=4[CH2:1]3)=[O:15])([CH3:31])[CH2:20][C:19]=2[C:21]=1[CH3:30]

参加物

5

反応物 2

HCID 5284359Calcium ChlorideHCID 68846049(+/-)-(1,3,4,9-Tetrahydro-beta-carboline-2-yl)-(5-nitro-2,4,6,7-tetramethyldihydrobenzofuran-2-yl)methanone

生成物 1

HCID 23118280(+/-)-(5-Amino-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran-2-yl)-(1,3,4,9-tetrahydro-beta-carboline-2-yl)-methanone収率 38.1%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 702Ethanol溶媒

実験手順

0.54 g of (±)-(1,3,4,9-tetrahydro-beta-carboline-2-yl)-(5-nitro-2,4,6,7-tetramethyldihydrobenzofuran-2-yl)methanone, 1.86 g of zinc, 0.19 g of calcium chloride dehydrate and 30 ml of ethanol were added, followed by heating at reflux overnight. The insoluble matter was filtered through celite and the solvent was distilled off. The reaction solution was mixed with water, extracted with 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:ethyl acetate=50:1) to obtain 0.19 g of the objective product (melting point: 129-133° C.)

後処理

  1. temperatureby heating
  2. temperatureat reflux overnight
  3. filtrationThe insoluble matter was filtered through celite
  4. distillationthe solvent was distilled off
  5. additionThe reaction solution was mixed with water
  6. extractionextracted with chloroform
  7. washwashed with saturated saline
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationafter the solvent was distilled off under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (chloroform:ethyl acetate=50:1)

出典と根拠

ORDレコード
ord-025cdb3cfeb84dca8c23b45e09e29315
出典データセット
uspto-grants-2009_06
特許番号
US07553837B2

反応ノート

読み込み中…