N,N,N',N'-Tetramethylethylenediamine → HCID 66638798, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-tert-butyl-2-methyl-6-trifluoromethyl-nicotinamide (2.3 g, 8.7 mmol) and TMEDA (2.7 mL, 17 mmol) in 130 mL of THF at −68° C. is slowly added LDA (2M, 8.7 mL, 17.4 mmol). The reaction temperature is maintained at −68° C., then warmed to −20° C. and is then immediately re-cooled to −68° C. To the reaction is added a solution of [(R)-2-(2,5-difluoro-phenyl)-1-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester (1 g, 2.9 mmol) in 20 mL of THF over a period of 10 minutes. The reaction is allowed to stir an additional 20 min after which the reaction is poured into 150 mL of a chilled 3% (w/v) solution of NaHSO4 in water. The solution is adjusted to pH7 by addition of pH7 buffer and the product is extracted into dichloromethane. The organic phase is dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification of the resultant residue by silica gel flash column chromatography provides the title compound.

Provenance & Evidence