Lithium Hydroxide → 5-(1,1-Dimethylethyl) 6,7-dihydroisoxazolo[4,5-c]pyridine-3,5(4H)-dicarboxylate

HRID 2388693Notes

Reaction equation

HRID 2388693 reaction equation
[OH-].[Li+].[O:3]1[C:11]2[CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7][C:6]=2[C:5]([C:19]([O:21]CC)=[O:20])=[N:4]1>C(O)C>[C:15]([O:14][C:12]([N:8]1[CH2:9][CH2:10][C:11]2[O:3][N:4]=[C:5]([C:19]([OH:21])=[O:20])[C:6]=2[CH2:7]1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 576186205-(1,1-Dimethylethyl) 3-ethyl 6,7-dihydroisoxazolo[4,5-c]pyridine-3,5(4H)-dicarboxylate

Product 1

HCID 576186225-(1,1-Dimethylethyl) 6,7-dihydroisoxazolo[4,5-c]pyridine-3,5(4H)-dicarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An aqueous lithium hydroxide solution (0.54 g, 12.88 mol in 12.8 ml) was added dropwise to a solution of 5-tert-butyl 3-ethyl 6,7-dihydroisoxazolo[4,5-c]pyridine-3,5(4H)-dicarboxylate (3.2 g, 10.73 mmol) in ethanol (48 ml) at 0° C. and the mixture was stirred at room temperature for 3 hours. The mixture was then concentrated in vacuo, the residue was acidified with 10% strength citric acid and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried with Na2SO4, filtered and concentrated in vacuo. The crude product was employed directly in the next stage without further purification.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. extractionthe mixture was extracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was employed directly in the next stage without further purification

Sources & evidence

ORD record
ord-a9e22ff8c5194fc8972603269962041e
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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