Trifluoroacetic acid → 2-Methyl-4-p-tolyl-2,7-diazaspiro[4.5]decan-1-one

HRID 1036730Notes

Reaction equation

HRID 1036730 reaction equation
[CH3:1][N:2]1[CH2:6][CH:5]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)[C:4]2([CH2:18][CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]2)[C:3]1=[O:26].C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[CH3:1][N:2]1[CH2:6][CH:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][CH:12]=2)[C:4]2([CH2:18][CH2:17][CH2:16][NH:15][CH2:14]2)[C:3]1=[O:26]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 71060320HCID 71060320, compound

Product 1

HCID 710606252-Methyl-4-p-tolyl-2,7-diazaspiro[4.5]decan-1-oneYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
7.5 °C

Procedure

To a stirred solution of tert-butyl 2-methyl-1-oxo-4-p-tolyl-2,7-diazaspiro[4.5]decane-7-carboxylate (270 mg, 0.753 mmol) in DCM (5 ml) at 5° C. was added TFA (870 ul, 11.30 mmol) and the reaction mixture was left to stir at 5-10° C. for 1 hr. The reaction mixture was added to 2M NaOH (5 ml) and extracted with DCM (3×5 ml). The organics were combined, washed with brine (5 ml), dried (MgSO4) and concentrated to give the crude product as a white solid (176 mg).

Workup

  1. waitthe reaction mixture was left
  2. extractionextracted with DCM (3×5 ml)
  3. washwashed with brine (5 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-689ec6dac4984f19a7eb1fba73590797
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

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