Ethanol → 3-pentyl-L-phenylalanine

To a 300 mL Parr bottle were added 0.41 g of PdCl2, 1.36 g of (2R,3S,5S)-6-oxo-2,3-diphenyl-5-(3-(3-pentyl)benzyl)morpholine, 50 mL of EtOH, and 30 mL of THF. The mixture was deoxygenated by bubbling nitrogen through for 10 min and was hydrogenated at 45 psi for 18 h. The vessel was purged with nitrogen, catalyst removed by filtration through celite, and the filtrate concentrated in vacuo to a volume of 15 mL. The solution was chilled in an ice bath and triturated with addition of 50 mL of hexane. A fine precipitate slowly formed. After storing at 5° C. overnight, the solid was collected by filtration and dried in vacuo to afford 0.65 g (72%) of 3-(3-pentyl-L-phenylalanine.HCl as a white powder, m.p. 170° C. (dec).

1. customThe mixture was deoxygenated
2. customby bubbling nitrogen through for 10 min
3. customThe vessel was purged with nitrogen, catalyst
4. customremoved by filtration through celite
5. concentrationthe filtrate concentrated in vacuo to a volume of 15 mL
6. temperatureThe solution was chilled in an ice bath
7. customtriturated with addition of 50 mL of hexane
8. customA fine precipitate slowly formed
9. waitAfter storing at 5° C. overnight
10. filtrationthe solid was collected by filtration
11. customdried in vacuo

ORD record

ord-dc36d81969cd4f31a67c6e18e3f3c21b

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06319702B1