Tert-butyl 2-(6-chloro-1H-indol-3-YL)ethylcarbamate → [2-(6-Chloro-1h-indol-3-yl)ethyl](methyl)amine

HRID 1666794ノート

反応式

HRID 1666794 の反応式
C(O[C:6]([NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=O)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:6][NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[NH:13][CH:12]=1

参加物

4

反応物 2

HCID 21071680Tert-butyl 2-(6-chloro-1H-indol-3-YL)ethylcarbamateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 21071655[2-(6-Chloro-1h-indol-3-yl)ethyl](methyl)amine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Combine N-t-butoxycarbonyl-2-(6-chloro-1H-indol-3-yl)ethylamine (1.3 g, 4.41 mmol) and dry THF (20 ml) and add dropwise to an ice bath cooled suspension of LiAlH4 (1.0 g, 26.5 mmol) in dry THF (30 ml). Heat to reflux. After 2 hours, cool to, ambient temperature and stir. After 15 hours, quench with saturated NaSO4 (100 ml/mol), stir for 1 hour at ambient temperature, then filter under vacuum. Wash precipitate with THF and evaporated filtrate and washes to residue. Chromatograph the residue on silica gel eluting with dichloromethane/2N NH3(methanol) (84/16) to give the title compound: MS (ACPI): m/e 209.0 (M+1).

後処理

  1. temperaturecooled
  2. temperatureHeat to reflux
  3. waitAfter 15 hours
  4. customquench with saturated NaSO4 (100 ml/mol)
  5. stirringstir for 1 hour at ambient temperature
  6. filtrationfilter under vacuum
  7. washWash precipitate with THF
  8. customevaporated filtrate and washes to residue

出典と根拠

ORDレコード
ord-020ffdc7da214bce874e21803db1a669
出典データセット
uspto-grants-2011_10
特許番号
US08044090B2

反応ノート

読み込み中…