Sulfuric acid magnesium salt (1:1) → N-{3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(1E)-3-methoxyprop-1-en-1-yl]benzyl}cyclopropanamine

HRID 658239Notes

Reaction equation

HRID 658239 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15](/[CH:17]=[CH:18]/[CH2:19][O:20][CH3:21])[CH:16]=1)[CH:12]=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH:22]1([NH2:25])[CH2:24][CH2:23]1.S([O-])([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>C(Cl)Cl.CO>[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15](/[CH:17]=[CH:18]/[CH2:19][O:20][CH3:21])[CH:16]=1)[CH2:12][NH:25][CH:22]1[CH2:24][CH2:23]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 69828CyclopropylamineHCID 4311764Sodium borohydrideHCID 86635919HCID 86635919, compound

Product 1

HCID 66761765N-{3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(1E)-3-methoxyprop-1-en-1-yl]benzyl}cyclopropanamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(1E)-3-methoxyprop-1-en-1-yl]benzaldehyde (1 eq.) from the previous step in DCM was added cyclopropanamine (2 eq.) and magnesium sulfate (1.5 eq.). The resulting suspension was stirred at rt for 12 h. The insolubles were removed via filtration. Concentration of the filtrate in vacuo afforded the crude imine as a yellow oil. This was then taken up in methanol (0.3 M), and then sodium borohydride (1.5 eq.) was added portionwise at 0° C. over 5 min. The reaction mixture was slowly warmed to rt over 1 h and then stirred at it for 2 h. The reaction was slowly quenched with saturated aqueous NaHCO3 solution, and the resulting mixture was extracted with ether. The combined organic extracts were washed with water, brine, dried over MgSO4, and concentrated in vacuo to afford the title compound as a golden, yellow oil.

Workup

  1. customThe insolubles were removed via filtration
  2. customConcentration of the filtrate in vacuo afforded the crude imine as a yellow oil
  3. temperatureThe reaction mixture was slowly warmed to rt over 1 h
  4. stirringstirred at it for 2 h
  5. customThe reaction was slowly quenched with saturated aqueous NaHCO3 solution
  6. extractionthe resulting mixture was extracted with ether
  7. washThe combined organic extracts were washed with water, brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-81d4611d30c2475b8caad05c82385973
Source dataset
uspto-grants-2011_12
Patent number
US08076359B2

Reaction notes

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