2,6-Lutidine → N-{[1-(3-methoxypropyl)-4-methyl-1H-indol-3-yl]methyl}cyclopropanamine

HRID 872031ノート

反応式

HRID 872031 の反応式
FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[CH:13]1([N:16]([CH2:24][C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][C:32]=3[CH3:34])[N:27]([CH2:35][CH2:36][CH2:37][O:38][CH3:39])[CH:26]=2)C(=O)OC(C)(C)C)[CH2:15][CH2:14]1.N1C(C)=CC=CC=1C.C(=O)(O)[O-].[Na+]>ClCCl.CO>[CH3:39][O:38][CH2:37][CH2:36][CH2:35][N:27]1[C:28]2[C:33](=[C:32]([CH3:34])[CH:31]=[CH:30][CH:29]=2)[C:25]([CH2:24][NH:16][CH:13]2[CH2:14][CH2:15]2)=[CH:26]1

参加物

7

反応物 4

HCID 79372,6-LutidineHCID 65367Trimethylsilyl triflateHCID 516892Sodium BicarbonateHCID 59494370tert-butyl cyclopropyl{[1-(3-methoxypropyl)-4-methyl-1H-indol-3-yl]methyl}carbamate

生成物 1

HCID 59494170N-{[1-(3-methoxypropyl)-4-methyl-1H-indol-3-yl]methyl}cyclopropanamine

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

Trimethylsilyl trifluoromethanesulfonate (213 μL) was added to a solution of tert-butyl cyclopropyl{[1-(3-methoxypropyl)-4-methyl-1H-indol-3-yl]methyl}carbamate (175 mg and 2,6-lutidine (192 μL) in dichloromethane (7 ml) under ice-cooling and the mixture was stirred at room temperature for 15 minutes. A saturated aqueous solution of sodium bicarbonate and methanol were added successively to the reaction mixture and the mixture was further stirred at the same temperature for 30 minutes. The reaction mixture was extracted with chloroform and the organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated in vacuo. The resulted residue was purified with a silica gel column chromatography (eluting solvent: ethyl acetate/methanol=95/5 to 70/30) to give N-{[1-(3-methoxypropyl)-4-methyl-1H-indol-3-yl]methyl}cyclopropanamine (106 mg) as a colorless oil.

後処理

  1. temperaturecooling
  2. stirringthe mixture was further stirred at the same temperature for 30 minutes
  3. extractionThe reaction mixture was extracted with chloroform
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulted residue was purified with a silica gel column chromatography (eluting solvent: ethyl acetate/methanol=95/5 to 70/30)

出典と根拠

ORDレコード
ord-636f8f88832f4dfa8e4f04df3e8783b5
出典データセット
uspto-grants-2015_03
特許番号
US08975252B2

反応ノート

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