Methanol → HCID 58071486, compound

To a solution of cis-4-benzylamino-1-tert-butoxycarbonyl-3-fluoropiperidine (0.9087 g, 2.95 mmol) in anhydrous dichloromethane (5 mL) under argon was added trifluoroacetic acid (2.5 mL) and the solution was stirred at room temperature under argon for 140 min. Anhydrous methanol (1 mL) was added and the solvents were removed in vacuo. More methanol (2 mL) was added and removed in vacuo. The residue was partitioned between CH2Cl2 (30 mL) and dilute NaOH solution (20 mL). The aqueous layer was further extracted with CH2Cl (30 ml×2) and the combined organic extracts were washed with brine (50 mL), dried (Na2SO4) and evaporated in vacuo to give 0.5756 g (94%) of the title compound as a colourless oil. δH (250 MHz, CDCl3) 1.54 (1H, qd, J=12.0 and 4.1 Hz), 1.83 (1H, m), 2.54-2.76 (3H, m), 3.11 (1H, m), 3.88 (2H, m), 4.73 (1H, m), 7.23-7.37 (5H, m).

1. customthe solvents were removed in vacuo
2. additionMore methanol (2 mL) was added
3. customremoved in vacuo
4. customThe residue was partitioned between CH2Cl2 (30 mL) and dilute NaOH solution (20 mL)
5. extractionThe aqueous layer was further extracted with CH2Cl (30 ml×2)
6. washthe combined organic extracts were washed with brine (50 mL)
7. dry with materialdried (Na2SO4)
8. customevaporated in vacuo

ORD record

ord-febf5c510381488382c0aa4873e83db9

Source dataset

uspto-grants-1998_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05837715