Reaktion #704520

Reaktionsgleichung

3-(2-(S)-azetidinylmethoxy)-5-bromopyridine

HCHO

NaBH3CN

→

title compound

3-((1-methyl-2-(S)-azetidinyl)methoxy)-5-bromopyridine

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvents were removed under reduced pressure
2. 2
   ExtraktionThe mixture was extracted with methylene chloride
3. 3
   Trocknenthe extract was dried over MgSO4
4. 4
   Sonstigethe solvent was removed
5. 5
   SonstigeThe residue was purified by chromatography on silica gel
6. 6
   Wascheneluting with 200:1 and 100:1 chloroform

Vorschrift

A 480 mg sample of the free base of 3-(2-(S)-azetidinylmethoxy)-5-bromopyridine, from Example 67 above, was dissolved in 4 mL of acetic acid treated with 1 mL of 37% HCHO and 500 mg of NaBH3CN at 0° C. for 4 hr. The solvents were removed under reduced pressure. The residue was basified with NaHCO3 solution. The mixture was extracted with methylene chloride, the extract was dried over MgSO4, and the solvent was removed. The residue was purified by chromatography on silica gel, eluting with 200:1 and 100:1 chloroform:methanol to give 68 mg of the title compound. MS (DCI/NH3) m/e: 257/259 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 8.28 (d, J=1.9 Hz, 1H), 8.26 (d, J=2.6 Hz, 1H), 7.38 (dd, J=1.9, 2.6 Hz, 1H), 4.02 (d, J=6.3 Hz, 2H), 3.51-3.44 (m, 1H), 3.43-3.37 (m, 1H), 2.93-2.84 (m, 1H), 2.41 (s, 3H), 2.13-2.03 (m, 2H).

Quelle