HCID 10591945, compound → HCID 10513010, compound

10% Palladium on carbon catalyst (640 mg) was added to an ethanol (15 ml) solution of 3-(S)-tert-butoxycarbonylamino-4-(S)-fluoromethyl-N-[1-(R)-phenylethyl]pyrrolidine (644 mg, 2.00 mmol), and the mixture was subjected to 2 hours of catalytic hydrogenation at 50° C. After removal of the catalyst by filtration, the solvent in the resulting filtrate was evaporated, and the thus obtained residue was mixed with 10% citric acid aqueous solution and washed with dichloromethane (15 ml×3) and diethyl ether (15 ml×1). The aqueous layer was adjusted to pH 10 to 11 with 1N sodium hydroxide aqueous solution and then extracted with chloroform (50 ml×4). The organic layer was dried over sodium sulfate, the solvent was evaporated and then the resulting residue was purified by recrystallizing it from a chloroform-n-hexane mixed solvent to give 344 mg (79%) of the title compound in the form of white crystals.

1. customAfter removal of the catalyst
2. filtrationby filtration
3. customthe solvent in the resulting filtrate was evaporated
4. additionthe thus obtained residue was mixed with 10% citric acid aqueous solution
5. washwashed with dichloromethane (15 ml×3) and diethyl ether (15 ml×1)
6. extractionextracted with chloroform (50 ml×4)
7. dry with materialThe organic layer was dried over sodium sulfate
8. customthe solvent was evaporated
9. customthe resulting residue was purified
10. customby recrystallizing it from a chloroform-n-hexane mixed solvent

ORD record

ord-9776ae3f67b547af81b42f26b341869c

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06656952B2