HCID 68542752, compound → HCID 68542021, compound

Participants

Reaction Steps

A solution of 90 mg (0.21 mmol) 2-but-3-enylamino-6-methoxy-N-[3-methyl-1-(4-methyl-5-oxo-tetrahydro-furan-2-yl)-hept-6-enyl]-isonicotinamide in 6 ml DCM is added dropwise over 30 min to a refluxing solution of 3.5 mg tricyclohexylphosphine [1,3-bis(2,4,6-trimethyl-phenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV)dichloride(‘Grubbs second generation catalyst’) in 6 ml DCM and then stirred for 1 h at reflux. LC/MS shows that only little product has been formed, therefore, 7 mg catalyst are added and the mixture stirred for 18 h at reflux. Again, 11 mg catalyst are added and heating continued for 4 h. The reaction mixture is directly chromatographed on silica gel and eluted with DCM/MeOH 98:2 to yield the title compound (mixture of diastereomers) as a greenish foam.

Provenance & Evidence