Diisopropylethylamine → 3-methoxy-N-[(3R)-1-methylpyrrolidin-3-yl]-4-nitro-benzamide

3-methoxy-4-nitro-benzoyl chloride (Intermediate 189; 374 mg, 1.73 mmol) was dissolved in DCM (20 mL) and N,N-diisopropylethylamine (0.96 mL, 5.54 mmol) added. The mixture was cooled in an ice/water bath and (3R)-1-methylpyrrolidin-3-amine dihydrochloride (Intermediate 184; 300 mg, 1.73 mmol) in DCM (10 mL) added dropwise. The mixture was allowed to warm to room temperature and stirred for 0.5 hour. The mixture was washed with brine, 2N NaOH(aq), dried with MgSO4 and evaporated to yield the title compound as a brown solid (227 mg, 46.9%).

1. temperatureThe mixture was cooled in an ice/water bath
2. washThe mixture was washed with brine, 2N NaOH(aq)
3. dry with materialdried with MgSO4
4. customevaporated

ORD record

ord-ceb02e1255be4dd89cc2316532daad46

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07709471B2