Formaldehyde → HCID 44325491, compound

To 164 mg (1 mmol) of 3-(3-(R)-pyrrolidinyloxy)-pyridine were added 300 mg (10 mmol) of paraformaldehyde, 314 mg (5 mmol) of NaCNBH3, and 5 mL of dry THF at room temperature. To the suspension was added 2 mL of trifluoroacetic acid dropwise. The suspension was allowed to stir at room temperature overnight. Next day, to the suspension was slowly added a mixture containing 20 mL of 4N NaOH and ice-chips. The mixture was then extracted with ethyl acetate (2×40 mL). The combined organic layers were dried over Na2SO4, and concentrated under reduced pressure. The crude product was purified by flash chromatography (15:1, CHCl3:MeOH) to obtain 9 mg (5%) of a clear oil: 1H NMR (300 MHz, CD3OD) δ 8.19 (1H, d, J=1.7 Hz), 8.12 (1H, m). 7.38 (2H, m), 4.99 (1H, m), 2.94-2.80 (3H, m), 2.52-1.93 (3H, m), 2.40 (3H, s); Mass spectrum (ESI) m/z 179.4 (M+H+).

1. additionNext day, to the suspension was slowly added a mixture
2. extractionThe mixture was then extracted with ethyl acetate (2×40 mL)
3. dry with materialThe combined organic layers were dried over Na2SO4
4. concentrationconcentrated under reduced pressure
5. customThe crude product was purified by flash chromatography (15:1, CHCl3:MeOH)

ORD record

ord-761904fd05b149ceb81418cec9549504

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06888001B2