Water → (+/-)-2-Propionyl-2-azabicyclo[2.2.1]hept-5-en-3-one
Reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[C:3](=[O:8])[NH:2]2.N1C=CC=CC=1.[C:15](Cl)(=[O:18])[CH2:16][CH3:17].O>C(#N)C>[C:15]([N:2]1[C:3](=[O:8])[CH:4]2[CH2:7][CH:1]1[CH:6]=[CH:5]2)(=[O:18])[CH2:16][CH3:17]Participants
6
Procedure
47 g of (±)-2-azabicyclo[2.2.1]hept-5-en-3-one were dissolved in acetonitrile (325 ml) and pyridine (41 ml) under nitrogen. At 12° C., 43.9 g of propionyl chloride were added dropwise over the course of 1 h. The reaction was then stirred at room temperature for 5 h. 145 ml of water were added to the mixture, and the acetonitrile was evaporated off in vacuo. The aqueous phase was extracted 3 times with 115 ml of ethyl acetate. The combined organic phases were washed with 1N HCl (140 ml), saturated NaHCO3 (40 ml) and NaCl (40 ml) solutions, dried with sodium sulphate and completely evaporated. The residue was purified by distillation. 55.8 g of title compound were obtained and solidified on leaving to stand. The yield was 81.6%.
Workup
- customthe acetonitrile was evaporated off in vacuo
- extractionThe aqueous phase was extracted 3 times with 115 ml of ethyl acetate
- washThe combined organic phases were washed with 1N HCl (140 ml), saturated NaHCO3 (40 ml) and NaCl (40 ml) solutions
- dry with materialdried with sodium sulphate
- customcompletely evaporated
- distillationThe residue was purified by distillation
Sources & evidence
- ORD record
- ord-0c3136aad15d41338df21b5a5c1e8c7a
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07405065B2
Reaction notes
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