Sulfuric acid magnesium salt (1:1) → N-[3-[(1E)-3-Methoxyprop-1-en-1-yl]-5-(trifluoromethyl)benzyl]cyclopropanamine

HRID 337643Notes

Reaction equation

HRID 337643 reaction equation
[CH3:1][O:2][CH2:3]/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1)[CH:9]=O.[CH:18]1([NH2:21])[CH2:20][CH2:19]1.[O-]S([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>C(Cl)Cl.CO.C1COCC1>[CH3:1][O:2][CH2:3]/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1)[CH2:9][NH:21][CH:18]1[CH2:20][CH2:19]1

Participants

8

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 69828CyclopropylamineHCID 4311764Sodium borohydrideHCID 866516823-[(1E)-3-Methoxyprop-1-en-1-yl]-5-(trifluoromethyl)benzaldehyde

Product 1

HCID 67062106N-[3-[(1E)-3-Methoxyprop-1-en-1-yl]-5-(trifluoromethyl)benzyl]cyclopropanamine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-[(1E)-3-Methoxyprop-1-en-1-yl]-5-(trifluoromethyl)benzaldehyde (1 eq.) from the previous step and cyclopropylamine (2 eq.) were combined in CH2Cl2 (0.2 M). To this was then added MgSO4 (1.5 eq.) and the resulting suspension was stirred at RT for 18 h. The insolubles were then removed via filtration through a pad of celite and the filtrate was concentrated in vacuo. The crude imine thus obtained was then re-taken up in a 2:1 (v/v) mixture of THF:MeOH (0.2 M). To this solution was added sodium borohydride (5 eq.) portionwise and the resulting mixture was stirred at RT for 18 h. The reaction was quenched with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The combined organic extracts were then washed with brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→EtOAc) afforded the title compound.

Workup

  1. customThe insolubles were then removed via filtration through a pad of celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe crude imine thus obtained
  4. customThe reaction was quenched with saturated aqueous sodium bicarbonate
  5. extractionextracted with ethyl acetate
  6. washThe combined organic extracts were then washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated in vacuo
  10. customPurification of the crude product by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→EtOAc)

Sources & evidence

ORD record
ord-092aa81d5a854ccea7e5b152928344f0
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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