反応 #42721

反応方程式

Sodium borohydride

scopolamine

hydrochloric acid

→

title compound

収率 50.0%

9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-ol

収率 50.0%

溶媒

ethanol

diethyl ether

反応条件

後処理

1. 1
   workup.STIRRINGstirred for another 24 h at ambient temperature
2. 2
   ろ過The reaction mixture was filtered
3. 3
   洗浄the resulting solid was washed with diethyl ether
4. 4
   workup.DISSOLUTIONThe dried solid was dissolved in the minimum amount of 10% aqueous potassium carbonate solution
5. 5
   抽出extracted with trichloromethane (6×150 mL)
6. 6
   乾燥The combined organic extracts were dried (magnesium sulfate)
7. 7
   ろ過filtered
8. 8
   その他the solvent was removed under reduced pressure

実験手順

Sodium borohydride (39.0 g, 1.03 mol) was added portionwise to a stirred suspension of scopolamine (75 g, 171 mmol) in ethanol (743 mL), at 0° C. under a nitrogen atmosphere and the reaction mixture was stirred at ambient temperature for 24 h. The mixture was then acidified with 2M hydrochloric acid in diethyl ether (600 mL) and stirred for another 24 h at ambient temperature. The reaction mixture was filtered and the resulting solid was washed with diethyl ether. The dried solid was dissolved in the minimum amount of 10% aqueous potassium carbonate solution and extracted with trichloromethane (6×150 mL). The combined organic extracts were dried (magnesium sulfate), filtered and the solvent was removed under reduced pressure to give the title compound as crystals (13.2 g, 85.5 mmol, 50%).

出典