1,1'-Carbonyldiimidazole → HCID 19029344, compound

Participants

Reaction Steps

Treat the acid from Step 4 (9.3 g) in EtOAc (100 mL) with 1,1'-carbonyldiimidazole (4.62 g) and DMAP (345 mg), stir the resulting solution at room temperature for 15 min., then heat at 50° C. for 1 h. Cool the reaction mixture to 0° C. and treat with a solution of NaBH4 (3.45 g) in H2O (50 mL), warm slowly to room temperature and stir for 12 h. Dilute the reaction mixture with EtOAc (250 mL) and wash with 1N HCl (1×100 mL) and H2O (1×100 mL), dry over MgSO4, filter and concentrate under reduced pressure to yield a crude oil (13 g). Chromatograph on silica gel, eluting with 5% CH3 OH/CH2Cl2 to give 3,4-dichloro-β-(2-hydroxyethyl)-N-methyl-N-[(2-methoxyphenyl) methyl]benzenepropanamide (8.7 g). HRMS (FAB, M+H+): m/e cal'd for [C20H24NO3Cl2 ]+ 396.1133; found 396.1124.

Provenance & Evidence