Hydrochloric Acid → HCID 53777216, compound

Participants

Reaction Steps

To a solution of (2R,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-(pyrimidin-5-ylmethyl)pyrrolidine (29.1 g) in methanol (146 ml) was added concentrated hydrochloric acid (12.9 ml) at 5° to 7° C. After the reaction mixture was stirred for an hour at room temperature, 28% sodium methoxide in methanol (29.7 ml) was dropped thereto at 5° C. to 10° C., and then the solution was stirred for 30 minutes at 10° C. Insoluble material was removed by filtration, then the filtrate was concentrated. Acetonitrile (120 ml) was added to the residue, and the mixture was stirred with magnesium sulfate. Magnesium sulfate was removed by filtration and the filtrate was concentrated until the volume amounted to 60 ml. Heptane (80 ml) was added thereto, and the acetonitrile layer was washed with Heptane (80 ml) four times. The acetonitrile layer was evaporated under reduced pressure and then the residue was distilled off with toluene (20 ml) to give (2R,4R)-1-allyloxycarbonyl-4-hydroxy-2-(pyrimidin-5-ylmethyl) pyrrolidine (24.1 g) as an oil.

Provenance & Evidence