Trifluoroacetic acid → 3-Methyl-1-phenyl-1,3,7-triaza-spiro[4.5]decan-4-one

HRID 1036719Notes

Reaction equation

HRID 1036719 reaction equation
C(OC([N:8]1[CH2:25][CH2:24][CH2:23][C:10]2([N:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:13][N:12]([CH3:21])[C:11]2=[O:22])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:21][N:12]1[C:11](=[O:22])[C:10]2([CH2:23][CH2:24][CH2:25][NH:8][CH2:9]2)[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 710601793-Methyl-4-oxo-1-phenyl-1,3,7-triaza-spiro[4.5]decane-7-carboxylic acid tert-butyl ester

Product 1

HCID 710602063-Methyl-1-phenyl-1,3,7-triaza-spiro[4.5]decan-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methyl-4-oxo-1-phenyl-1,3,7-triaza-spiro[4.5]decane-7-carboxylic acid tert-butyl ester (70 mg, 0.2 mmol) in DCM (5 ml) was added TFA (0.5 ml, 6.5 mmol). The reaction mixture was stirred at RT for 1 hour before applying the reaction mixture to a 1 g SCX-2 cartridge. Impurities were eluted with 1:1 DCM:MeOH, followed by 0.05 M ammonia in 1:1 DCM:MeOH. Product was eluted with 1M ammonia in 1:1 DCM:MeOH. The clean fractions were concentrated in vacuo to afford the title compound. No further purification was performed on the title compound.

Workup

  1. washImpurities were eluted with 1:1 DCM
  2. washProduct was eluted with 1M ammonia in 1:1 DCM
  3. concentrationThe clean fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-001045ec4d5346559106c2e06ebdb8f3
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

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