Lithium iodide → HCID 53779416, compound

Participants

Reaction Steps

To a solution of (2S,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-(3-methoxy-3-oxo-1-propenyl)pyrrolidine (18.7 g) in tetrahydrofuran (190 ml) were added successively sodium borohydride (3.83 g) and lithium iodide (13.5 g) at room temperature and the mixture was refluxed for 4 hours. After cooling to room temperature, the mixture was diluted with water (200 ml) and extracted with ethyl acetate (200 ml×3). The combined extracts were washed with brine (400 ml), dried over magnesium sulfate and concentrated to give (2R,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-(3-hydroxypropyl)pyrrolidine (17.2 g) as a pale yellow paste.

Provenance & Evidence