Triethylamine → HCID 11703167, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (1R,2R)-2-(2-bromophenyl)-5,5-difluorocyclohexanecarboxylic acid (820 mg, 2.58 mmol), benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (1.49 g, 2.86 mmol) and aminoacetonitrile hydrochloride (530 mg, 5.73 mmol) in N, N-dimethylformamide (5.0 mL) was cooled to 0° C. and treated with triethylamine (1.26 mL, 9.04 mmol). The resulting slurry was stirred at room temperature for 2.5 hours and then poured into water and extracted with ethyl acetate (3×). The combined extracts were washed with brine and dried (Na2SO4). Concentration in vacuo and chromatography of the residue on silica eluting with 2/3 EtOAc/hexanes yielded (1R,2R)-2-(2-bromophenyl)-N-(cyanomethyl)-5,5-difluorocyclohexanecarboxamide as a faint-yellow foam.

Provenance & Evidence