2,5-Difluorobenzaldehyde → HCID 11479096, compound

Participants

Reaction Steps

To 643 mg (1.3 mmol) (2S,4R)-C-[1-(5-Propyl-pyrimidin-2-yl)-4-tritylsulfanyl-pyrrolidin-2-yl]-methylamine in 3 ml methanol were added 158 μl (1.43 mmol) 2,5-difluorobenzaldehyde and 5 ml methanol to partially redissolve the compound. This was followed by a solution of 108 mg (0.78 mmol) zinc chloride and 109 mg (1.56 mmol) NaBH3CN in 3 ml methanol. The solution was stirred over night, concentrated and dissolved in ETOAc/sat NaHCO3 solution. The inorganic layer was extracted with EtOAc, the combined organic layers were washed with NaHCO3 and brine, dried over Na2SO4 and evaporated. Purification with column chromatography yielded 750 mg (93%) (2S,4R)-(2,5-Difluoro-benzyl)-[1-(5-propyl-pyrimidin-2-yl)-4-tritylsulfanyl-pyrrolidin-2-ylmethyl]-amine as light yellow gum, MS: 621 (MH+).

Provenance & Evidence