Ethyl 4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)benzoate → Ethyl 4-(4-oxopiperidin-1-yl)benzoate

HRID 1785787Notes

Reaction equation

HRID 1785787 reaction equation
O1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[O:4]CC1>C(O)(=O)C>[O:4]=[C:5]1[CH2:6][CH2:7][N:8]([C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=2)[CH2:9][CH2:10]1

Participants

3

Reactant 1

HCID 12717439Ethyl 4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)benzoate

Product 1

HCID 12717442Ethyl 4-(4-oxopiperidin-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of Example 158A (6.31g, 21.7 mmol) and 30% aqueous acetic acid (100 mL) in TMF (50 mL) was stirred at 95° C. for 6 hours, cooled to room temperature, concentrated, treated with water, and extracted with dichloromethane. The combined extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated to provide the desired product. MS (DCI) m/e 248 (M+H)+.

Workup

  1. concentrationconcentrated
  2. additiontreated with water
  3. extractionextracted with dichloromethane
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fbd7aa398c044336aeb90159ac2f3fe7
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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