N-{3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(1E)-3-methoxyprop-1-en-1-yl]benzyl}cyclopropanamine → N-[3-{[tert-Butyl(dimethyl)silyl]oxy}-5-(3-methoxypropyl)benzyl]cyclo-propanamine

HRID 658240Notes

Reaction equation

HRID 658240 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:17]=[C:18](/[CH:20]=[CH:21]/[CH2:22][O:23][CH3:24])[CH:19]=1)[CH2:12][NH:13][CH:14]1[CH2:16][CH2:15]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:17]=[C:18]([CH2:20][CH2:21][CH2:22][O:23][CH3:24])[CH:19]=1)[CH2:12][NH:13][CH:14]1[CH2:16][CH2:15]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

4

Reactant 1

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

Product 1

HCID 57956095N-[3-{[tert-Butyl(dimethyl)silyl]oxy}-5-(3-methoxypropyl)benzyl]cyclo-propanamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-{3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(1E)-3-methoxyprop-1-en-1-yl]benzyl}cyclopropanamine from the previous step (1 eq.) in EtOAc (0.04 M) was added 10% palladium on activated carbon (10 mol %). The vessel was evacuated and back filled with hydrogen. The reaction suspension was then stirred under a balloon atmosphere of hydrogen for 1.5 h. The reaction was diluted with DCM and filtered through a bed of celite. The insolubles were further washed with EtOAc and methanol. Concentration of the filtrate in vacuo afforded the title compound amine 1 as a colorless oil.

Workup

  1. customThe vessel was evacuated
  2. additionback filled with hydrogen
  3. additionThe reaction was diluted with DCM
  4. filtrationfiltered through a bed of celite
  5. washThe insolubles were further washed with EtOAc and methanol

Sources & evidence

ORD record
ord-0fc402729f62494dbac4ddb15f973dba
Source dataset
uspto-grants-2011_12
Patent number
US08076359B2

Reaction notes

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