Sodium Hydroxide → [3-(5-Methoxy-benzofuran-2-yl)-3-phenyl-propyl]-methyl-amine

HRID 250195

反応式

HRID 250195 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][CH:9]=[CH:8][C:7]=2[CH:11]=1.[CH3:12][N:13](C(=O)C(F)(F)F)[CH2:14][CH2:15][CH:16](OC(=O)C(F)(F)F)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:15][CH2:14][NH:13][CH3:12])=[CH:8][C:7]=2[CH:11]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 259435-MethoxybenzofuranHCID 58088435HCID 58088435、化合物

生成物 1

HCID 11623507[3-(5-Methoxy-benzofuran-2-yl)-3-phenyl-propyl]-methyl-amine

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
110 °C

実験手順

5-methoxybenzofuran (0.48 g) and trifluoro-acetic acid 3-[methyl-(2,2,2-trifluoro-acetyl)-amino]-1-phenyl-propyl ester (0.48 g) were mixed and heated in a sealed tube at 110° C. for 90 minutes. Upon cooling, the reaction mixture was taken up in methanol and treated with excess 1N sodium hydroxide solution, sufficient to form a strongly basic solution. After stirring for 20 minutes, the reaction mixture was concentrated at reduced pressure to remove the bulk of the methanol. The resulting mixture was partitioned between ethyl acetate and water. The layers were separated and the organic layer was evaporated to dryness. Purification by column chromatography (silica gel, dichloromethane (130):methanol (10):ammonium hydroxide (1)) followed by preparative tlc afforded [3-(5-Methoxy-benzofuran-2-yl)-3-phenyl-propyl]-methyl-amine (M+H=296) as the major component.

後処理

  1. temperatureUpon cooling
  2. customsufficient to form a strongly basic solution
  3. concentrationthe reaction mixture was concentrated at reduced pressure
  4. customto remove the bulk of the methanol
  5. customThe resulting mixture was partitioned between ethyl acetate and water
  6. customThe layers were separated
  7. customthe organic layer was evaporated to dryness
  8. customPurification by column chromatography (silica gel, dichloromethane (130):methanol (10):ammonium hydroxide (1))

出典と根拠

ORDレコード
ord-8bfd3924d9a14e69914d03f9d7cc7dba
出典データセット
uspto-grants-2011_01
特許番号
US07863305B2

関連ノート

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