Tryptophol → N-[1-(1,3,4,9-Tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)ethyl]acetamide

HRID 647587ノート

反応式

HRID 647587 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][OH:12])=[CH:2]1.[CH3:13][CH:14]([NH:18][C:19](=[O:21])[CH3:20])[C:15](=O)[CH3:16]>B(F)(F)F.CCOCC.C1C=CC=CC=1>[CH3:16][C:15]1([CH:14]([NH:18][C:19](=[O:21])[CH3:20])[CH3:13])[C:2]2[NH:1][C:9]3[C:4]([C:3]=2[CH2:10][CH2:11][O:12]1)=[CH:5][CH:6]=[CH:7][CH:8]=3

参加物

5

反応物 2

HCID 10685TryptopholHCID 97923N-(1-methyl-2-oxopropyl)acetamide

生成物 1

HCID 12708188N-[1-(1,3,4,9-Tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)ethyl]acetamide

試薬・触媒・溶媒 2

HCID 8000Boron trifluoride etherate触媒HCID 241Benzene溶媒

実験手順

A mixture of indole-3-ethanol (16.1 g), benzene (1200 ml), N-(1-methyl-2-oxopropyl)-acetamide[12.7 g, described by A. Triebs and W. Sutter, Chem. Ber. 84, 96(1951)] and boron trifluoride-etherate (5 drops) is refluxed using a water separating condenser for 60 minutes. After cooling, the mixture is washed with concentrated sodium bicarbonate, dried over magnesium sulfate and evaporated. The residue is chromatographed on silica gel using chloroform. The eluates are evaporated to give a residue of the title compound as a 1:1 mixture of diastereoisomers:

後処理

  1. customfor 60 minutes
  2. temperatureAfter cooling
  3. washthe mixture is washed with concentrated sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue is chromatographed on silica gel
  7. customThe eluates are evaporated

出典と根拠

ORDレコード
ord-95788004af7e4f22990074913ccd93f3
出典データセット
uspto-grants-1983_10
特許番号
US04409224

反応ノート

読み込み中…