Trifluoroacetic acid → 4-(4-Fluorophenyl)-2-((5-methylisoxazol-3-yl)methyl)-2,7-diazaspiro[4.5]decan-1-one

HRID 1036726Notes

Reaction equation

HRID 1036726 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:12]3([CH2:17][CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13]3)[C:11](=[O:25])[N:10]([CH2:26][C:27]3[CH:31]=[C:30]([CH3:32])[O:29][N:28]=3)[CH2:9]2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:12]3([CH2:17][CH2:16][CH2:15][NH:14][CH2:13]3)[C:11](=[O:25])[N:10]([CH2:26][C:27]3[CH:31]=[C:30]([CH3:32])[O:29][N:28]=3)[CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71060659Tert-butyl 4-(4-fluorophenyl)-2-((5-methylisoxazol-3-yl)methyl)-1-oxo-2,7-diazaspiro[4.5]decane-7-carboxylate

Product 1

HCID 710604374-(4-Fluorophenyl)-2-((5-methylisoxazol-3-yl)methyl)-2,7-diazaspiro[4.5]decan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 4-(4-fluorophenyl)-2-((5-methylisoxazol-3-yl)methyl)-1-oxo-2,7-diazaspiro[4.5]decane-7-carboxylate (243.6 mg; 0.549 mmol) was solubilised in DCM (1 ml). Trifluoroacetic acid (0.86 ml; 11.14 mmol) was added and the mixture stirred at RT for 20 minutes before being concentrated in vacuo. The oil was dissolved with methanol (5 ml) and passed through a 10 g SCX-2 cartridge eluting with 2M NH3 in methanol (50 ml) and concentrated in vacuo to yield the title compound.

Workup

  1. concentrationbefore being concentrated in vacuo
  2. dissolutionThe oil was dissolved with methanol (5 ml)
  3. washeluting with 2M NH3 in methanol (50 ml)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ccde26696944a359733b9d4fc5b15e0
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

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