Sodium Hydroxide → (2S)-N-ethyl-2-(4-fluorophenyl)pent-4-en-1-amine

HRID 749458노트

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HRID 749458 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([NH:9][C:10](=O)[C@H:11]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[CH2:12][CH:13]=[CH2:14])[CH3:8].[OH-].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>CCOCC.C(Cl)Cl.O>[CH2:7]([NH:9][CH2:10][C@H:11]([C:15]1[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=1)[CH2:12][CH:13]=[CH2:14])[CH3:8]

참가 물질

8

반응물 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 68978786(2S)-N-ethyl-2-(4-fluorophenyl)pent-4-enamide

생성물 1

HCID 68978108(2S)-N-ethyl-2-(4-fluorophenyl)pent-4-en-1-amine수율 100%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매2회HCID 6344Dichloromethane용매

실험 절차

LiAlH4 (36 mg, 0.95 mmol) was added to ether (5 mL) at 0° C. under nitrogen. (2S)-N-Ethyl-2-(4-fluorophenyl)pent-4-enamide (140 mg, 0.63 mmol), dissolved in ether (2 mL) was added and the mixture was stirred overnight at room temperature. Water (0.04 mL) was added followed by an aqueous solution of NaOH (0.16 mL, 1M) and the mixture stirred for 30 min. Celite®, MgSO4 and CH2Cl2 was added and the solid material removed by filtration. The solvent was removed by evaporation and there was obtained 0.13 g (100%) of (2S)-N-ethyl-2-(4-fluorophenyl)pent-4-en-1-amine. 1H NMR (500 MHz, CDCl3): 1.0 (m, 3H), 2.2-2.9 (m, 5H), 3.2-3.4 (m, 2H), 4.9-5.1 (m, 2H), 5.6-5.7 (m, 1H), 7.0-7.4 (m, 4H). LCMS: m/z 208 (M+1)+.

후처리

  1. additionwas added
  2. stirringthe mixture stirred for 30 min
  3. customthe solid material removed by filtration
  4. customThe solvent was removed by evaporation

출처 및 근거

ORD 기록
ord-8712a9c8497c437d84c4dfb22c9d9c8b
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402581B2

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