Ethanol → Diethylamine

Participants

Reaction Steps

The title compound was prepared (as a mixture of two enantiomers) from 1-(3-methylpyrrolidin-3-yl)-4-phenylpiperidine and 2-(3,4-dichlorobenzamido)acetic acid using general procedure G. HPLC (Table 1, Method b) Rt 2.13 min; m/z: (M+H)+ 474. From the mixture, the enantiomers were isolated via chiral preparative RP-HPLC (isocratic 10% methanol:10% ethanol:80% heptane:0.2% diethylamine modifier at 15 mL/min, column temperature 50° C.; UV detection monitored at 254 nm; Daicel OD-H column, 20×250 mm, 5 um particle) to yield two isomers, (S)- and (R)-3,4-dichloro-N-(2-(3-methyl-3-(4-phenylpiperidin-1-yl)pyrrolidin-1-yl)-2-oxoethyl)benzamide. The absolute stereochemistry of the isomers was not assigned. Isomer 1 eluted at Rt 11.5-14 min. Isomer 2 eluted at Rt 14.8-18 min.

Provenance & Evidence