Trifluoroacetic acid → 3-[(3S)-3-Pyrrolidinyloxy]pyridine

Temperature

2.5 °C

Under a nitrogen atmosphere, a cold (0-5° C.), stirring solution of 3-((3S)-N-(tert-butoxycarbonyl)-3-pyrrolidinyloxy)pyridine (0.535 g, 2.024 mmol) in dry CH2Cl2 (5 mL, distilled from LiAlH4) was treated drop-wise with trifluoroacetic acid (3 mL, 4.44 g, 38.94 mmol). After stirring 30 min at 0-5° C., the solution was concentrated by rotary evaporation. The residue was acidified with 1 M HCl solution (15 mL) and extracted with toluene (4×25 mL) to remove impurities (triphenylphosphine oxide). At 0-5° C., the aqueous layer was basified with 1 M NaOH solution to pH 12. The mixture was saturated with NaCl and extracted with CHCl3 (8×20 mL). The combined CHCl3 extracts were dried (Na2SO4), filtered, concentrated by rotary evaporation and briefly dried under high vacuum to give 240 mg (72.3%) of a light-yellow oil.

1. concentrationthe solution was concentrated by rotary evaporation
2. extractionextracted with toluene (4×25 mL)
3. customto remove impurities (triphenylphosphine oxide)
4. customAt 0-5° C.
5. extractionextracted with CHCl3 (8×20 mL)
6. dry with materialThe combined CHCl3 extracts were dried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated by rotary evaporation
9. custombriefly dried under high vacuum

ORD record

ord-37a766cbc03148c2b88c0d35565badf4

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06627648B1