Water → Benzyl 9-oxo-3-azaspiro(5.5)undec-7-ene-3-carboxylate

HRID 1253671Notes

Reaction equation

HRID 1253671 reaction equation
[CH:1]([C:3]([CH3:5])=[O:4])=[CH2:2].O.[CH:7]([CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:11][CH2:10]1)=O.[OH-].[K+]>C(O)C>[O:4]=[C:3]1[CH2:5][CH2:7][C:9]2([CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[O:16])[CH2:11][CH2:10]2)[CH:2]=[CH:1]1

Participants

6

Reactant 4

HCID 962Water2×HCID 6570Methyl vinyl ketoneHCID 14797Potassium HydroxideHCID 2776272Benzyl 4-formylpiperidine-1-carboxylate

Product 1

HCID 23435732Benzyl 9-oxo-3-azaspiro(5.5)undec-7-ene-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Methyl vinyl ketone (1.64 ml), ethanol (5 ml) and water (5 ml) were added to benzyl 4-formylpiperidine-1-carboxylate (5 g). The mixture was then added to a boiling solution of potassium hydroxide (0.22 g) in ethanol (10 ml) and the resulting reaction mixture was refluxed for 1 h (TLC control). When the reaction was complete, the mixture was added to water (25 ml) and extracted with ethyl acetate (2×50 ml). The combined organic phases were dried (Na2SO4) and concentrated in vacuo. The crude product obtained in this way was purified by column chromatography (silica gel, 25% ethyl acetate/hexane). Yield: 2.8 g (46%)

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 1 h (TLC control)
  3. extractionextracted with ethyl acetate (2×50 ml)
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-42f0456a8a0c49c8b6c2451fc354fb71
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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