Acetic Anhydride → HCID 66679631, compound

HRID 474137Notes

Reaction equation

HRID 474137 reaction equation
[N:1]12[CH2:9][CH:5]([CH2:6][CH2:7][CH2:8]1)[CH:4]([OH:10])[CH2:3][CH2:2]2.[C:11](OC(=O)C)(=[O:13])[CH3:12]>>[N:1]12[CH2:9][CH:5]([CH2:6][CH2:7][CH2:8]1)[CH:4]([O:10][C:11](=[O:13])[CH3:12])[CH2:3][CH2:2]2

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 189861071-Azabicyclo[3.3.1]nonan-4-ol

Product 1

HCID 66679631HCID 66679631, compoundYield 87%

Conditions

Temperature
120 °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 reextracted 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.

Workup

  1. temperatureunder cooling
  2. customis evaporated
  3. extractionextracted with THF/
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. distillationThe crude product is purified by bulb-to-bulb distillation (HV, 90° C.)

Sources & evidence

ORD record
ord-fc88957f041f4360bd0aa07fb16a65f0
Source dataset
uspto-grants-2014_01
Patent number
US08637517B2

Reaction notes

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