Ethyl benzoylformate → HCID 178472739, compound

Participants

Reaction Steps

A solution of 300 mg (1.0 mmol) of the acetate salt of 2-(4-amino-cyclohexyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol (example 2.1) in 5 mL of EtOH was treated with 227 mg (1.0 mmol) of oxo-phenyl-acetic acid ethyl ester and with 87 mg (1.0 mmol) of sodium cyanoborohydride. The mixture was stirred overnight at RT and distributed between a saturated aqueous solution of NaHCO3 and Et2O. Drying of the combined organic phases over Na2SO4 and chromatography on silica gel with heptane/EtOAc 4:1 yielded ca. 100 mg (25%) of cis phenyl-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-cyclohexylamino]-acetic acid ethyl ester and ca. 100 mg (25%) of trans phenyl-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-cyclohexylamino]-acetic acid ethyl ester as a colorless oil, MS: 428 (M+H)+.

Provenance & Evidence