Trifluoroacetic acid → Ethyl 4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxylate

HRID 2388692Notes

Reaction equation

HRID 2388692 reaction equation
FC(F)(F)C(O)=O.N1([C:13]23[O:28][N:27]=[C:26]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:14]2[CH2:15][N:16](C(OC(C)(C)C)=O)[CH2:17][CH2:18]3)CCCC1.C([O-])(O)=O.[Na+]>>[O:28]1[C:13]2[CH2:18][CH2:17][NH:16][CH2:15][C:14]=2[C:26]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[N:27]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 685054785-tert-Butyl 3-ethyl 7a-(pyrrolidin-1-yl)-3a,4,7,7a-tetrahydroisoxazolo[4,5-c]pyridine-3,5(6H)-dicarboxylate

Product 1

HCID 44558551Ethyl 4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxylate

Conditions

Temperature
0 °C

Procedure

Trifluoroacetic acid (6.67 ml, 89.9 mmol) was added to a solution of 5-tert-Butyl 3-ethyl 7a-(pyrrolidin-1-yl)-3a,4,7,7a-tetrahydroisoxazolo[4,5-c]pyridine-3,5(6H)-dicarboxylate (5.5 g, 14.98 mmol) in MC (100 ml) at 0° C. and the mixture was stirred under reflux for 16 hours. Thereafter, the mixture was cooled to 0° C. and NaHCO3 solution was added. The phases were separated and the aqueous phase was extracted with methylene chloride. The combined organic phases were dried with Na2SO4, filtered and concentrated in vacuo. The crude product obtained was employed directly in the next stage without further purification.

Workup

  1. temperatureunder reflux for 16 hours
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with methylene chloride
  4. dry with materialThe combined organic phases were dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f7ce032ce1504454b12d5f5d9ef0361e
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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