Trifluoroacetic anhydride → Tetrahydropyridino[1,2-c][1,2,3]oxadiazolone

HRID 2216564Notes

Reaction equation

HRID 2216564 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[N:14]([N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]1[C:22]([OH:24])=[O:23])=O>C1COCC1>[NH:14]1[N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]2[C:22](=[O:23])[O:24]1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 20614N-Nitrosopipecolic acid

Product 1

HCID 69656246Tetrahydropyridino[1,2-c][1,2,3]oxadiazolone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoroacetic anhydride (1.93 g) was added to the THF (92 mL) solution of crude (2RS)-1-nitrosopiperidine-2-carboxylic acid under a nitrogen atmosphere at 0° C. and stirred for 5 h at 0° C. and for 2 h at room temperature. The solution was concentrated under a reduced pressure. The residue was applied to silica gel column chromatography, then the column was eluted with n-hexane-AcOEt (1/1–0/1). The titled compound was obtained as colorless crystals (1.10 g, 33%).

Workup

  1. concentrationThe solution was concentrated under a reduced pressure
  2. washthe column was eluted with n-hexane-AcOEt (1/1–0/1)

Sources & evidence

ORD record
ord-9ff03be4fa564273b043f6d90e3253ea
Source dataset
uspto-grants-2006_09
Patent number
US07112582B2

Reaction notes

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