Di-tert-butyl dicarbonate → tert-Butyl 5-iodoisoindoline-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of the product of Step A (0.77 g; 2.15 mmol) and (BOC)2O (0.7 g; 3.2 mmol) in anhydrous pyridine (3 ml) was stirred for 1 h at ˜70° C. After removing solvents under reduced pressure, the residue was diluted to 20 ml with Et2O. The insoluble material was filtered off, and filtrate was washed with diluted HCl (5 ml), saturated NaHCO3 (5 ml), brine and dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2; CH2Cl2:hexane 1:1) to give title compound (0.58 g; 78%) as creamy oil. 1H-NMR (CDCl3) 1.49 (5, 9H); 4.58-4.63 (m, 4H); 6.9-7.04 (m, 1H); 7.5-7.63 (m, 2H).

Provenance & Evidence