1,1'-Carbonyldiimidazole → 3,4-Dichloro-beta-(2-hydroxyethyl)-N-methyl-N-(phenylmethyl)benzenepropanamide

3,4-Dichloro-beta-[2-[(phenylmethyl)methylamino]-2-oxoethyl]benzenepropanoic acid (6.9 g) in EtOAc (150 mL) was treated with carbonyldiimidazole (4.4 g) and N,N-dimethylaminopyridine (0.22 g). The resulting solution was stirred at room temperature for 15 minutes and then heated at 50° C. for 1 hour. The reaction mixture was cooled to 0° C. and treated with a solution of NaBH4 (4.46 g) in H2O (75 mL), warmed slowly to room temperature and stirred for 12 hours. The reaction mixture was then diluted with EtOAc (250 mL) and washed with 1N HCl (250 mL), H2O (250 mL) and dried over MgSO4, filtered and concentrated under reduced pressure to yield the title compound (6.29 g).

1. temperatureheated at 50° C. for 1 hour
2. temperatureThe reaction mixture was cooled to 0° C.
3. temperaturewarmed slowly to room temperature
4. stirringstirred for 12 hours
5. washwashed with 1N HCl (250 mL), H2O (250 mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-134fadaa76494e69ad4d76e6b7e8b8d7

Source dataset

uspto-grants-1997_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05654316