Trifluoroacetic acid → 2-Methyl-4-phenyl-2,8-diazaspiro[4.6]undecan-1-one

HRID 1036708Notes

Reaction equation

HRID 1036708 reaction equation
[CH3:1][N:2]1[CH2:6][CH:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]2([CH2:18][CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)[C:3]1=[O:26].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][N:2]1[CH2:6][CH:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]2([CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:3]1=[O:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71060314Tert-butyl 2-methyl-1-oxo-4-phenyl-2,8-diazaspiro[4.6]undecane-8-carboxylate

Product 1

HCID 710605462-Methyl-4-phenyl-2,8-diazaspiro[4.6]undecan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A diastereomeric mixture of tert-butyl 2-methyl-1-oxo-4-phenyl-2,8-diazaspiro[4.6]undecane-8-carboxylate (step 4) (683.1 mg; 1.906 mmol) in DCM (6 ml) was treated with TFA (5.8 ml, 76 mmol) and stirred at RT for 10 minutes. The mixture was concentrated in vacuo and the crude product was dissolved in MeOH and applied to a 10 g pre-wetted (MeOH) SCX-2 cartridge. The column was washed with MeOH and the product was eluted with 2M NH3 in MeOH. The clean fractions were concentrated in vacuo to afford the title compound;

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe crude product was dissolved in MeOH
  3. washThe column was washed with MeOH
  4. washthe product was eluted with 2M NH3 in MeOH
  5. concentrationThe clean fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-db267e25f8a342568ff8cd2bdc581362
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

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