Reaktion #669000

Reaktionsgleichung

NaOH

Formic acid

formaldehyde

3-(3-pyridyl)-2-azabicylo[2.2.2]octane

(+/-)-3-(3-pyridyl)-2-azabicyclo[2.2.2]octane

→

(+/-)-2-methyl-3-(3-pyridyl)-2-azabicylo[2.2.2]octane

Ausbeute 88.0%

(±)-2-Methyl-3-(3-pyridyl)-2-azabicylo[2.2.2]octane

Ausbeute 88.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturrefluxed for 24 hours under N2
2. 2
   workup.ADDITIONbasified by addition of a solution of 40%
3. 3
   Extraktionextracted with chloroform (4×10 mL)
4. 4
   TrocknenThe combined extracts were dried over anhydrous K2CO3
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   workup.DISTILLATIONThe resulting oil was purified by distillation under reduced pressure (116°-118° C./0.4 mm Hg)

Vorschrift

Formic acid (5 mL, 95-97%) and formaldehyde (0.5 mL, 37%) were added to 3-(3-pyridyl)-2-azabicylo[2.2.2]octane (XIII) (170 mg) and refluxed for 24 hours under N2. The reaction mixture was cooled to 0° C. (ice bath), basified by addition of a solution of 40% w/v NaOH in water (pH=9) and extracted with chloroform (4×10 mL). The combined extracts were dried over anhydrous K2CO3, filtered and concentrated. The resulting oil was purified by distillation under reduced pressure (116°-118° C./0.4 mm Hg) to give 160 mg (88%) of (+/-)-2-methyl-3-(3-pyridyl)-2-azabicylo[2.2.2]octane (XV). 1H NMR(CDCl3): δ 8.85 (s, 1H), 8.80-8.10 (d, 1H), 7.78-7.71 (m, 1H), 7.23-7.20 (m, 1H),4.70 (s, 1H), 3.60 (s, 1H), 2.5 (s, 3H), 2.25 (s, 1H), 2.20-1.95 (m, 2H), 1.80-1.69 (m, 3H), 1.50-1.42 (m, 3H).

Quelle