Trifluoroacetic acid → Ethyl 3-hydroxy-4-oxopiperidine-1-carboxylate

HRID 38531Notes

Reaction equation

HRID 38531 reaction equation
[OH:1][CH:2]1[C:7](OC)([O:8]C)[CH2:6][CH2:5][N:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:3]1.FC(F)(F)C(O)=O>C1COCC1>[OH:1][CH:2]1[C:7](=[O:8])[CH2:6][CH2:5][N:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 3019465Ethyl 3-hydroxy-4,4-dimethoxypiperidine-1-carboxylate

Product 1

HCID 58116852Ethyl 3-hydroxy-4-oxopiperidine-1-carboxylateYield 117.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-hydroxy-4,4-dimethoxypiperidine-1-carboxylate from Example 34A (5.00 g, 21.4 mmol) was dissolved in THF (50 mL), and trifluoroacetic acid (15.9 mL, 214 mmol) was added. The mixture was stirred for 3.5 h at rt. The solvent was then removed in vacuo. Twice, toluene was added and again removed in vacuo. The residue was dissolved in dichloromethane, dried over sodium sulfate, and the solvent was removed in vacuo to yield 4.70 g (95%) of an oil, which was used without further purification.

Workup

  1. customThe solvent was then removed in vacuo
  2. additionTwice, toluene was added
  3. customagain removed in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0f23eb935e624549bb2a1931a2483b84
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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