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

HRID 1848442Notes

Reaction equation

HRID 1848442 reaction equation
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]2)[CH2:5][CH2:4][N:3]1[C:19]1[CH2:20][O:21][C:22](=[O:24])[CH:23]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[O:24]=[C:22]1[O:21][CH2:20][C:19]([N:3]2[CH2:4][CH2:5][C:6]3([CH2:7][CH2:8][NH:9][CH2:10][CH2:11]3)[C:2]2=[O:1])=[CH:23]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86709449Tert-butyl 1-oxo-2-(5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 867094502-(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 1-oxo-2-(5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate (5.70 g, 16.9 mmol) in methylene chloride (10 mL) was added trifluoroacetic acid (26.1 mL, 339 mmol) and the resulting solution was stirred at rt for 1 h. After concentration the residue was basified on ion exchange column followed by washing with 1N ammonia in methanol solution to give 2-(5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one. LC/MS: (M+1)+: 237.06.

Workup

  1. concentrationAfter concentration the residue
  2. washby washing with 1N ammonia in methanol solution

Sources & evidence

ORD record
ord-44b6a5158029453a82e9a693b3245f26
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

Loading…