Trifluoroacetic acid → 2-(4-Ethyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

HRID 1848454Notes

Reaction equation

HRID 1848454 reaction equation
[CH2:1]([C:3]1[C:7](=[O:8])[O:6][CH2:5][C:4]=1[N:9]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)[C:10]1=[O:26])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([C:3]1[C:7](=[O:8])[O:6][CH2:5][C:4]=1[N:9]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[C:10]1=[O:26])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86709462HCID 86709462, compound

Product 1

HCID 867094632-(4-Ethyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(4-ethyl-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (0.34 g, 0.93 mmol) in dichloromethane (1 mL) was added trifluoroacetic acid (2.16 mL, 28 mmol) and the resulting solution was stirred at rt for 1 h. After removing the volatiles, the residue was dissolved in dichloromethane (2 mL) and treated with hydrogen chloride (2 mL, 4 N in dioxane) and the mixture was concentrated to give 2-(4-ethyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one. LC/MS: (M+1)+: 265.16.

Workup

  1. customAfter removing the volatiles
  2. dissolutionthe residue was dissolved in dichloromethane (2 mL)
  3. additiontreated with hydrogen chloride (2 mL, 4 N in dioxane)
  4. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-cda34c4b44204c45a1fa5ef185b6c7ef
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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