Dichloromethane → HCID 178501490, compound

Participants

Reaction Steps

To a mixture of methyl 2(R)-amino-3-(pyridin-2-ylmethylsulfanyl)propionate hydrochloride (1.31 g, 5 mmol), 2,2,2-trifluoro-1-(4-fluorophenyl)ethanone (0.875 g), DIPEA (2.39 g, 18.5 mmol), in dichloromethane (20 mL) was added titanium tetrachloride (4.65 mmol) dropwise over 5 min. After stirring for 3 h at ambient temperature, additional titanium tetrachloride (0.3 mmol) was added. After an additional hour of stirring, NaCNBH4 (0.973 g, 15.5 mmol) was added in methanol (10 mL). After 1 h, the reaction mixture was diluted with ethyl acetate (200 mL) and poured onto magnesium sulfate. After filtration and concentration, the residue was purified by flash chromatography to afford methyl 3-(pyridin-2-yl-methylsulfanyl)-2(R)-[2,2,2-trifluoro-1(RS)-(4-fluorophenyl)ethylamino]-propionate (640 mg, 1.59 mmol).

Provenance & Evidence