Potassium Carbonate → (S)-1-(4-bromophenyl)-N-(2-(2-isopropyl-1,3-dioxolan-2-yl)ethyl)ethanamine

HRID 80981

반응식

HRID 80981 반응식
[CH:1]([C:4]1([CH2:9][CH2:10]OS(C)(=O)=O)[O:8][CH2:7][CH2:6][O:5]1)([CH3:3])[CH3:2].[Br:16][C:17]1[CH:22]=[CH:21][C:20]([C@@H:23]([NH2:25])[CH3:24])=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([C@@H:23]([NH:25][CH2:10][CH2:9][C:4]2([CH:1]([CH3:2])[CH3:3])[O:5][CH2:6][CH2:7][O:8]2)[CH3:24])=[CH:19][CH:18]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 852999(alphaS)-4-Bromo-alpha-methylbenzenemethanamineHCID 107051032-(2-Isopropyl-1,3-dioxolan-2-yl)ethyl methanesulfonate

생성물 1

HCID 58109166(S)-1-(4-bromophenyl)-N-(2-(2-isopropyl-1,3-dioxolan-2-yl)ethyl)ethanamine수율 38%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of methanesulfonic acid 2-(2-isopropyl-[1,3]dioxolan-2-yl)-ethyl ester (12 g, 50 mmol) and (S)-1-(4-bromophenyl)ethanamine (19.9 g, 100 mmol) in CH3CN (250 mL) was added K2CO3 (8 g, 58 mmol), and the mixture was refluxed for 10 h. The solution was filtered, and the filtrate was concentrated to afford the crude product, which was purified by column chromatography to give [(S)-1-(4-bromophenyl)-ethyl]-[2-(2-isopropyl-[1,3]dioxolan-2-yl)-ethyl]-amine (6.5 g, 38%).

후처리

  1. temperaturethe mixture was refluxed for 10 h
  2. filtrationThe solution was filtered
  3. concentrationthe filtrate was concentrated
  4. customto afford the crude product, which
  5. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-abbecd99663840539e4f37761a82b03f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846668B2

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