Hydrochloric Acid → HCID 54160796, compound

Participants

Reaction Steps

To a solution of (2R,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-(2-pyridylmethyl)pyrrolidine (4.88 g) in acetonitrile (50 ml) was added dropwise conc. hydrochloric acid (3.3 ml) at room temperature. The reaction mixture was stirred for 5 hours, then neutralized with saturated aqueous sodium bicarbonate and diluted with ethyl acetate. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated under reduced pressure to give (2R,4R)-1-allyloxycarbonyl-4-hydroxy-2-(2-pyridylmethyl) pyrrolidine (2.46 g). On the other hand the aqueous layer was extracted five times with chloroform. The combined chloroform layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure to give (2R,4R)-1-allyloxycarbonyl-4-hydroxy-2-(2-pyridylmethyl) pyrrolidine (0.23 g).

Provenance & Evidence