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

HRID 1666794노트

반응식

HRID 1666794 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-020ffdc7da214bce874e21803db1a669
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044090B2

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