Reaction #640614

Reaction equation

1-aza-bicyclo[3.3.1]nonan-4-ol

acetic anhydride

→

(4SR,5RS)-acetic acid 1-aza-bicyclo[3.3.1]non-4-yl ester

Yield 87.0%

Conditions

Workup

1. 1
   Temperatureunder cooling
2. 2
   Otheris evaporated
3. 3
   Extractionextracted with THF/
4. 4
   WashThe combined organic layers are washed with brine
5. 5
   Dryingdried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Otherevaporated
8. 8
   workup.DISTILLATIONThe crude product is purified by bulb-to-bulb distillation (HV, 90° C.)

Procedure

To acetic anhydride (150 ml) (4SR,5RS)-(1-aza-bicyclo[3.3.1]nonan-4-ol (21.34 g, 151 mmol) is added portionwise under cooling. The reaction mixture is heated to 120° C. for 2.5 h, is evaporated and extracted with THF/sat. K2CO3 soln. The aq. layer is reextiacted with THF. The combined organic layers are washed with brine, dried over Na2SO4, filtered and evaporated. The crude product is purified by bulb-to-bulb distillation (HV, 90° C.) to give 24.07 g (87%) of (4SR,5RS)-acetic acid 1-aza-bicyclo[3.3.1]non-4-yl ester.

Source