反応 #162600

反応方程式

DIPEA

3-(6-chloro-2-(4-nitrophenyl)pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane

3-[6-Chloro-2-(4-nitro-phenyl)-pyrimidin-4-yl]-8-oxa-3-aza-bicyclo[3.2.1]octane

8-Oxa-3-azabicyclo[3.2.1]octane, HCl

8-oxa-3-aza-bicyclo[3.2.1]octane hydrochloride

triethylamine

→

title compound

収率 39.0%

3,3′-(2-(4-Nitrophenyl)pyrimidine-4,6-diyl)bis(8-oxa-3-azabicyclo[3.2.1]octane)

収率 39.0%

溶媒

ethyl acetate

dioxane

反応条件

後処理

1. 1
   その他In a 100 mL round-bottomed flask was placed
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITwas continued at 80° C. for 64 hours
4. 4
   洗浄washed with sat NaHCO3
5. 5
   乾燥The organic phase was dried over MgSO4
6. 6
   ろ過filtered
7. 7
   濃縮concentrated
8. 8
   workup.ADDITIONThe crude product was added to a silica gel column
9. 9
   洗浄eluted with ethyl acetate in hexanes (10-50%)

実験手順

In a 100 mL round-bottomed flask was placed 3-(6-chloro-2-(4-nitrophenyl)pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane (13, 135 mg, 0.39 mmol) in dioxane (5 ml). 8-Oxa-3-azabicyclo[3.2.1]octane, HCl (2, 0.15 g, 1 mmol) and triethylamine (0.28 ml, 2 mmol) were added. The mixture was stirred at 80° C. for 16 hours. DIPEA was added (0.3 mL) and stirring was continued at 80° C. for 64 hours. The reaction mixture was diluted with ethyl acetate and washed with sat NaHCO3 followed by 0.1 N HCl. The organic phase was dried over MgSO4, filtered and concentrated. The crude product was added to a silica gel column and eluted with ethyl acetate in hexanes (10-50%) to give 65 mg of the title compound (0.15 mmol, 39%).

出典