Methanamine, N-methoxy-, hydrochloride (1:1) → N-Methoxy-N-methyl-3-(4-chlorophenyl)-2-(3-fluorophenyl)propanamide

To a suspension N-methoxy-N-methylamine hydrochloride (2.0 g, 21 mmol) in 50 mL CH2Cl2 at 0° C. was added dimethylaluminum chloride (1 M in hexane, 21 mL, 21 mmol). After stirring at room temperature for 1 h, a solution of methyl 3-(4-chlorophenyl)-2-(3-fluorophenyl)propionate (Step A, 2.0 g, 10 mmol) in CH2Cl2 (10 mL) was added, and the resulting mixture was stirred overnight. The reaction mixture was quenched by addition of MeOH (5 mL), and the resulting mixture was concentrated with silica gel (50 g). The material was loaded onto a silica gel column, which was eluted with 10% EtOAc in hexane to 2% ammonia in MeOH (2 M) in 10% EtOAc/hexane to give the title compound. 1H NMR (400 MHz, CD3OD): δ 7.35-6.90 (m, 8H), 4.39 (br, 1H), 3.41 (s, 3H), 3.38-3.30 (m, 1H), 3.08 (s, 3H), 2.92 (dd, 1H). LC-MS: m/e 322 (M+H)+ (3.6 min).

1. stirringthe resulting mixture was stirred overnight
2. customThe reaction mixture was quenched by addition of MeOH (5 mL)
3. concentrationthe resulting mixture was concentrated with silica gel (50 g)
4. washwas eluted with 10% EtOAc in hexane to 2% ammonia in MeOH (2 M) in 10% EtOAc/hexane

ORD record

ord-bdb3a302d9924d91aa890ebc3c4f8da6

Source dataset

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07390835B2