Hydrochloric Acid → HCID 53777216, compound

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.

1. stirringat 5° C. to 10° C., and then the solution was stirred for 30 minutes at 10° C
2. customInsoluble material was removed by filtration
3. concentrationthe filtrate was concentrated
4. additionAcetonitrile (120 ml) was added to the residue
5. stirringthe mixture was stirred with magnesium sulfate
6. customMagnesium sulfate was removed by filtration
7. concentrationthe filtrate was concentrated until the volume
8. additionHeptane (80 ml) was added
9. washthe acetonitrile layer was washed with Heptane (80 ml) four times
10. customThe acetonitrile layer was evaporated under reduced pressure
11. distillationthe residue was distilled off with toluene (20 ml)

ORD record

ord-9ea2b0e740384ded8e9e63fbca5cb0ec

Source dataset

uspto-grants-1997_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05608056