Sulfuric acid magnesium salt (1:1) → [(2S)-2-(4-Fluorophenyl)pent-4-en-1-yl]methylamine

HRID 429478Notes

Reaction equation

HRID 429478 reaction equation
[CH3:1][NH:2][C:3](=O)[C@H:4]([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[CH2:5][CH:6]=[CH2:7].[H-].[Al+3].[Li+].[H-].[H-].[H-].[O-]S([O-])(=O)=O.[Mg+2]>O1CCCC1>[CH3:1][NH:2][CH2:3][C@H:4]([C:8]1[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=1)[CH2:5][CH:6]=[CH2:7]

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 15536022(S)-2-(4-fluorophenyl)pent-4-enoic acid, N-methyl amideHCID 21226445Aluminium lithium hydride

Product 1

HCID 15536023[(2S)-2-(4-Fluorophenyl)pent-4-en-1-yl]methylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine (S)-2-(4-fluorophenyl)pent-4-enoic acid, N-methyl amide (3.1 g, 14.96 mmol) and tetrahydrofuran (35 mL). Cool in an ice bath, add a solution of lithium aluminum hydride (35 mL, 1.0 M in tetrahydrofuran, 35 mmol). After the addition is complete, heat the reaction mixture to reflux. After 2.5 hours, cool in an ice bath and carefully quench with water (1.3 mL), an aqueous 15% sodium hydroxide solution (1.3 mL), and then water (4 mL). Dilute the quenched reaction mixture with diethyl ether (75 mL) , add MgSO4, and stir. After 1 hour, filter through celite and rinse the solids with dichloromethane. Evaporate the filtrate in vacuo to give (S)-N-methyl-(2-(4-fluorophenyl)pent-4-enyl)amine: Rf=0.47 (silica gel, 18.5/1.5/0.2 dichloromethane/methanol/concentrated aqueous ammonia).

Workup

  1. temperatureCool in an ice bath
  2. additionAfter the addition
  3. temperatureheat the reaction mixture
  4. temperatureto reflux
  5. temperaturecool in an ice bath
  6. customcarefully quench with water (1.3 mL)
  7. additionDilute
  8. customthe quenched reaction mixture with diethyl ether (75 mL)
  9. waitAfter 1 hour
  10. filtrationfilter through celite
  11. washrinse the solids with dichloromethane
  12. customEvaporate the filtrate in vacuo

Sources & evidence

ORD record
ord-a3d39aa19cb34bd2b382eebe73cd5866
Source dataset
uspto-grants-2001_11
Patent number
US06316445B1

Reaction notes

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