HCID 69622564, compound → HCID 14110361, compound
Reaction equation
ClC(Cl)(Cl)COC([N:7]1[C:13]2[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:12]=2[C:11](=[O:20])[N:10]2[CH2:21][CH2:22][CH2:23][C@H:9]2[C@@H:8]1O)=O>C1COCC1.CCOC(C)=O>[CH3:19][O:18][C:16]1[CH:15]=[CH:14][C:13]2[N:7]=[CH:8][CH:9]3[CH2:23][CH2:22][CH2:21][N:10]3[C:11](=[O:20])[C:12]=2[CH:17]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
10% Cd/Pb couple (2.50 g, 20 mmol Cd) was added to a rapidly stirring solution of 95 (1.71 g, 4.03 mmol) in a mixture of THF (30 mL) and 1N NH4OAc (30 mL). Upon addition, the solution turned cloudy and after 2 hours TLC showed the reaction to be complete. The reaction mixture was diluted with EtOAc (150 mL) and dried over anhydrous MgSO4. The solids were filtered and rinsed with EtOAc (50 mL). Removal of excess solvent by rotary evaporation under reduced pressure afforded the product as a yellow solid (0.84 g, 3.6 mmol, 90%).