10-(4-Trifluoromethyl-phenyl)-1,4-dioxa-10-aza-dispiro[4.2.4.2]tetradecan-9-one → 2-(4-Trifluoromethyl-phenyl)-2-aza-spiro[4.5]decane-1,8-dione

HRID 2368803Notes

Reaction equation

HRID 2368803 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:22][CH2:21][C:11]3([CH2:20][CH2:19][C:14]4(OCC[O:15]4)[CH2:13][CH2:12]3)[C:10]2=[O:23])=[CH:5][CH:4]=1>O1CCCC1>[F:25][C:2]([F:1])([F:24])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:22][CH2:21][C:11]3([CH2:12][CH2:13][C:14](=[O:15])[CH2:19][CH2:20]3)[C:10]2=[O:23])=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 5822999310-(4-Trifluoromethyl-phenyl)-1,4-dioxa-10-aza-dispiro[4.2.4.2]tetradecan-9-one

Product 1

HCID 582301722-(4-Trifluoromethyl-phenyl)-2-aza-spiro[4.5]decane-1,8-dioneYield 83.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10-(4-Trifluoromethyl-phenyl)-1,4-dioxa-10-aza-dispiro[4.2.4.2]tetradecan-9-one (6.7 g) was dissolved in tetrahydrofuran (189 ml) aqueous hydrochloric acid solution (2M, 94.3 ml) was added and the mixture was stirred for 12 hours at RT. The reaction mixture was poured into ice/water and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated to give the title compound as a colorless foam (4.9 g). MS (m/e): 311 [M+].

Workup

  1. additionwas added
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b95afd29e8d649bf9c2708a14ec4b831
Source dataset
uspto-grants-2014_04
Patent number
US08703807B2

Reaction notes

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