Trifluoroacetic acid → HCID 86709448, compound

HRID 1501759Notes

Reaction equation

HRID 1501759 reaction equation
[O:1]=[C:2]1[O:6][CH2:5][C:4]([N:7]2[CH2:12][CH2:11][CH2:10][C:9]3([CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)[CH2:8]2)=[CH:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:8]1[C:9]2([CH2:13][CH2:14][NH:15][CH2:16][CH2:17]2)[CH2:10][CH2:11][CH2:12][N:7]1[C:4]1[CH2:5][O:6][C:2](=[O:1])[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86709447tert-Butyl 2-(5-oxo-2,5-dihydrofuran-3-yl)-2,9-diazaspiro[5.5]undecane-9-carboxylate

Product 1

HCID 86709448HCID 86709448, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 2-(5-oxo-2,5-dihydrofuran-3-yl)-2,9-diazaspiro[5.5]undecane-9-carboxylate (266 mg, 0.792 mmol) in DCM (2 mL) was added TFA (2 mL, 26.0 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1 h, then concentrated under reduced pressure, then placed on the high vacuum. The residue was dissolved in MeOH and loaded onto a 2 g Bond Elut SCX column (pre-rinsed with MeOH). These were rinsed with MeOH, and the product was eluted via 2M NH3 in MeOH to afford 4-(2,9-diazaspiro[5.5]undecan-2-yl)furan-2(5H)-one. LC/MS: [(M+1)]+=237

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in MeOH
  3. washloaded onto a 2 g Bond Elut SCX column (pre-rinsed with MeOH)
  4. washThese were rinsed with MeOH
  5. washthe product was eluted via 2M NH3 in MeOH

Sources & evidence

ORD record
ord-504f1d55422644d39f0502a95b24a03e
Source dataset
uspto-grants-2015_12
Patent number
US09206198B2

Reaction notes

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