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

HRID 561820Notes

Reaction equation

HRID 561820 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+]>ClCCl.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 from the previous step (1 eq.) in dichloromethane (0.5 M) was added cyclopropylamine (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 added at 0° C. sodium borohydride (1.5 eq.) portionwise over 5 min. The reaction mixture was slowly warmed to RT over 1 h and then stirred at RT for 2 h. After carefully quenching with sat. aq. NaHCO3, the resulting mixture was extracted with ether. The combined organic extracts were washed with water and brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded 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 RT for 2 h
  5. customAfter carefully quenching with sat. aq. NaHCO3
  6. extractionthe resulting mixture was extracted with ether
  7. washThe combined organic extracts were washed with water and brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered

Sources & evidence

ORD record
ord-144713f7e21f4df5889b8f0d43679128
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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