Methanol → HCID 58189016, compound

Participants

Reaction Steps

A solution of ((S)-ethyl 3-(2-benzyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)piperazin-1-yl)-3-oxopropanoate (96 mg, 0.20 mmol) and sodium borohydride (30 mg, 0.80 mmol) in THF (4 mL) was brought to reflux and MeOH (242 μL, 6.0 mmol) added drop-wise over a 1 h period. The reaction mixture was allowed to heat at reflux for an additional 16 h and then quenched with a few drops of a 1 N HCl solution. The reaction was partitioned between EtOAc (10 mL) and a saturated aqueous solution of NaHCO3 (10 mL). The organic extract was further washed with brine then dried over MgSO4, filtered, and evaporated to an oil that was purified by silica gel flash chromatography with EtOAc as eluant to afford the title compound as an oil (51 mg, 58%). LC/MS (Method A) 4.34 min, [M+1]+ 439.

Provenance & Evidence