Borane;tetrahydrofuran → HCID 86669376, compound

Participants

Reaction Conditions

Reaction Steps

Acid A136 3-(2-(4-cyano-1-((2R,3S)-2-propyl-1-(4-(trifluoromethyl)nicotinoyl)-3-(5-(trifluoromethyl)thiophen-3-yloxy)piperidine-3-carbonyl)piperidin-4-yl)phenyl)propanoic acid (10 mg, 13.3 μmol) was dissolved in THF (0.5 mL). The mixture was cooled to 0° C. and BH3.THF (30 μL, 27.9 μmol) was added dropwise under Ar. The reaction was warmed to 23° C. and was stirred overnight. The reaction mixture was quenched with 1 M NaOH and was concentrated. The crude residue was purified by reverse phase preparative HPLC to yield 4-(2-(3-hydroxypropyl)phenyl)-1-((2R,3S)-2-propyl-1-(4-(trifluoromethyl)nicotinoyl)-3-(5-(trifluoromethyl)thiophen-3-yloxy)piperidine-3-carbonyl)piperidine-4-carbonitrile A138. LC/MS RT (10 min method)=6.04 min. Mass observed: 737.25 (M+H).

Provenance & Evidence