Tetrahydrofuran → Methyl 3-(4-oxopiperidin-1-yl)benzoate

HRID 338672Notes

Reaction equation

HRID 338672 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH2:19][CH2:18][C:13]3(OCC[O:14]3)[CH2:12][CH2:11]2)[CH:5]=1.C1COCC1.C([O-])(O)=O.[Na+]>S(=O)(=O)(O)O.O>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH2:19][CH2:18][C:13](=[O:14])[CH2:12][CH2:11]2)[CH:5]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 60059302Methyl-3-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)benzoate

Product 1

HCID 60059322Methyl 3-(4-oxopiperidin-1-yl)benzoateYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of methyl-3-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-benzoate (3.85 g, 13.88 mmol) in 10% aqueous sulfuric acid (40 mL and THF (40 mL) was stirred at ambient temperature for 14 days. The reaction mixture was neutralized by cautious addition of NaHCO3 and simultaneously diluting with water. The aqueous mixture was extracted with EtOAc (2×75 mL) and the combined organic extracts were dried (MgSO4), filtered, and concentrated to give the title compound as an oil (2.75 g, 85%) which was used without further purification.

Workup

  1. extractionThe aqueous mixture was extracted with EtOAc (2×75 mL)
  2. dry with materialthe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3a17ec9750d04ccd86b4be8fa8f753d1
Source dataset
uspto-grants-2014_11
Patent number
US08889870B2

Reaction notes

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