Pilar García

Synthesis of a New Chiral Pyrrolidine

The synthesis of a new chiral pyrrolidine has been performed using 2,3-O-iso-propylidene-D-erythronolactol as a suitable starting material.

(2R,3S,4R)-3,4-Isopropyl-idenedi-oxy-2-(phenyl-sulfonyl-meth-yl)pyrrolidin-1-ol.

The title compound, C14H19NO5S, was prepared by nucleophilic addition of the lithium derivative of methylphenylsulfone to (3S,4R)-3,4-isopropylidenedioxypyrroline 1-oxide. There are four molecules in the asymmetric unit. The crystal structure determination confirms the configuration of the chiral centres as 2R,3S,4R. In the crystal, pairs of O—H⋯N hydrogen bonds link the molecules into dimers.

(3R,4S)-3,4-Isopropyl­idenedioxy-3,4-dihydro-2H-pyrrole 1-oxide

The title compound C7H11NO3 was prepared by intramolecular nucleophilic displacement of 2,3-O-iso-propylidene-d-erythronolactol. There are two molecules in the asymmetric unit, which are related by a pseudo-inversion centre. The crystal structure determination confirms unequivocally the configuration of the chiral centres as 3S,4R. In the crystal structure, intermolecular C—H⋯O interactions link the molecules (into infinite zigzag chains along the a axis.