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

HRID 749458Notes

Reaction equation

HRID 749458 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

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)+.

Workup

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

Sources & evidence

ORD record
ord-8712a9c8497c437d84c4dfb22c9d9c8b
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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