2,6-Dimethylphenol → HCID 131731125, compound

Participants

Reaction Steps

A mixture of (3-difluoromethyl-1-methyl-1H-pyrazol-4-yl)-((S)-(2-hydroxymethyl-pyrrolidin-1-yl)-methanone (2.0 g; 7.7 mmol), which was prepared as described in example P8, triphenylphosphine (2.1 g; 8.0 mmol) and 2,6-dimethylphenol (0.94 g; 7.7 mmol) in dry THF (30 ml) was cooled in an ice-bath. Diisopropyl azocarboxylate (1.60 g; 8.0 mmol) in dry THF (15 ml) was added dropwise, with stirring under nitrogen atmosphere over 10 minutes. The reaction mixture was stirred at ambient temperature for 6 hours. After removal of the solvent in vacuo, the residue (6.81 g) was purified by flash chromatography using silica gel (eluent: cyclo hexane/ethyl acetate 2:8). 1.31 g (46.8% of theory) of 3-difluoromethyl-1-methyl-1H-pyrazol-4-yl)-[(S)-2-(2,6-dimethyl-phenoxymethyl)-pyrrolidin-1-yl]-methanone (compound 1.225) was obtained in form of a white solid m.p. 137-140° C.

Provenance & Evidence