Trifluoroacetic acid → 2-Methyl-2,8-diazaspiro[4.5]decan-1-one

HRID 921941Notes

Reaction equation

HRID 921941 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][C:4]2([CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]2)[C:3]1=[O:19].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][N:2]1[CH2:6][CH2:5][C:4]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[C:3]1=[O:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58893162HCID 58893162, compound

Product 1

HCID 3270242-Methyl-2,8-diazaspiro[4.5]decan-1-oneYield 89.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-methyl-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (315 mg, 1.174 mmol) in DCM (5 mL) was added TFA (1.718 mL, 22.30 mmol) and the mixture was stirred at room temperature for 2 h. The reaction was concentrated under reduced pressure to obtain crude and purified by SCX cartridge, loading with MeOH, washed with additional MeOH. Product was recovered eluting with 2M NH3 in MeOH. Solvent evaporation gave 2-methyl-2,8-diazaspiro[4.5]decan-1-one (177 mg).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customto obtain crude
  3. custompurified by SCX cartridge
  4. washwashed with additional MeOH
  5. customProduct was recovered
  6. washeluting with 2M NH3 in MeOH
  7. customSolvent evaporation

Sources & evidence

ORD record
ord-7e9e8980a06c47dbbd3363eaf04aef7a
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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