(3aS,7aS)-5-[(S)-3,3,3-Trifluoro-2-methoxy-2-phenylpropanoyl]-2,3,4,5,6,7-hexahydro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one monohydrate

(3aS,7aS)-5-[(S)-3,3,3-Trifluoro-2-methoxy-2-phenylpropanoyl]-2,3,4,5,6,7-hexahydro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one monohydrate

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rac-Benzyl 3-oxohexahydro-1H-pyrrolo[3,4-c]pyridine-5(6H)-carboxylate was separated Nail Polish by chiral chromatography, and one of the enantiomers ([α]22D = +10°) was hydrogenated in the presence of Pd/C in methanol, producing octahydro-3H-pyrrolo[3,4-c]pyridin-3-one.The latter was reacted with (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl chloride [(R)-(−)-Mosher acid chloride], giving rise to the title compound, C17H19F3N2O3·H2O.The present structure established the absolute configuration of the pyrrolopiperidine fragment based on the known configuration of the (R)-Mosher acid chloride.The piperidine ring has a somewhat distorted chair conformation and is cis-fused with the five-membered envelope-shaped ring; the plane of the exocyclic amide bond is approximately orthogonal to the plane of the phenyl ring, making a dihedral angle of 82.31 (3)°.

The water molecule acts as an acceptor to the proton of the amino group in an N—H.O interaction, and as a double proton donor in O—H.O hydrogen bonds, Can Openers generating infinite bands along the a axis.