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

HRID 1452082Notes

Reaction equation

HRID 1452082 reaction equation
[N:1]([N:3]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:4]1[C:5]([OH:7])=[O:6])=O.FC(F)(F)C(O)=O>ClCCl>[NH:1]1[N:3]2[CH2:11][CH2:10][CH2:9][CH2:8][CH:4]2[C:5](=[O:7])[O:6]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20614N-Nitrosopipecolic acid

Product 1

HCID 69656246Tetrahydropyridino[1,2-c][1,2,3]oxadiazoloneYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-Nitrosopipecolinic acid (prepared by the method of W. Lijinsky, L. Keefer and J. Loo Tetrahedron 1970, 26, 5137) (1.82 g, 11.5 mM) in dichloromethane (15 ml) was cooled in ice and treated dropwise with trifluoroacetic acid (1.62 ml, 11.5mM). The mixture was stirred with cooling for 6 h then diluted with further dichloromethane, and washed with saturated aqueous sodium hydrogen carbonate solution until the washings were neutral. The organic phase was dried (MgSO4) and evaporated to give the title compound as a yellow oil (1.12 g, 76%): νmax (CH2Cl2) 1732 cm-1 ; δH (CDCl3) 1.90-2.02 (2H, m), 2.04-2.19 (2H, m), 2.63 (2H, t, d 6 Hz) and 4.25 (2H, t, J6 Hz); EI m/e 140 (93%).

Workup

  1. temperaturewith cooling for 6 h
  2. washwashed with saturated aqueous sodium hydrogen carbonate solution until the washings
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-a7dfb17b0584462e87f7ecdc6bc40286
Source dataset
uspto-grants-1997_02
Patent number
US05606051

Reaction notes

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