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

HRID 749458ノート

反応式

HRID 749458 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-8712a9c8497c437d84c4dfb22c9d9c8b
出典データセット
uspto-grants-2008_07
特許番号
US07402581B2

反応ノート

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