Diazomethane → HCID 59279850, compound

Participants

Reaction Conditions

Reaction Steps

Palladium acetate (0.67 g, 2.97 mol) and freshly prepared diazomethane (300 mL, 0.5 M solution in Et2O, 150 mmol) were added to a solution of the product from Step 3 (16.6 g, 29.7 mmol) in Et2O (300 mL) cooled to 0° C. After 15 minutes, N2 was bubbled through the mixture for 15 minutes, and the black mixture was filtered through CELITE with Et2O as the eluent. The solvent was removed in vacuo, and the residue was taken up in Et2O (300 mL) and cooled to 0° C. Palladium acetate (0.67 g, 2.97 mol) and freshly prepared diazomethane (100 mL, 0.5 M solution in Et2O, 50 mmol) were then added. After 15 minutes, N2 was bubbled through the mixture for 15 minutes, and the black mixture was filtered through CELITE with Et2O as the eluent. The solvent was removed in vacuo, and the residue was taken up in Et2O (300 mL) and cooled to 0° C. Palladium acetate (0.67 g, 2.97 mol) and freshly prepared diazomethane (100 mL, 0.5 M solution in Et2O, 50 mmol) were then added. After 15 minutes, N2 was bubbled through the mixture for 15 minutes, and the black mixture was filtered through CELITE with Et2O as the eluent. The solvent was removed in vacuo, and the crude product was purified on silica (gradient elution, 0-60% EtOAc/hexanes) to yield the title compound. LRMS ESI+ (M+H)+ 573.2, calcd for C31H45N2O8: 573.3.

Provenance & Evidence