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

HRID 553423Notes

Reaction equation

HRID 553423 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[O:14][N:15]=[C:16]([C:17]([O:19]CC)=[O:18])[C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[O:14][N:15]=[C:16]([C:17]([OH:19])=[O:18])[C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

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

A mixture of 7.31 g (25 mmol) of 6,7-dihydro-4H-isoxazolo[4,5-c]pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-tert-butyl ester (E), 43 g (30 mmol) of lithium hydroxide and 75 mL of EtOH was stirred at RT for 12 h. The solvent was removed under a vacuum and the residue redissolved in a mixture of water/citric acid (pH=4) and ether. The organic phase was separated off, dried over magnesium sulfate and the solvent was removed under a vacuum. 6.65 g (99% of theoretical) of the desired product 6,7-dihydro-4H-isoxazolo[4,5-c]pyridine-3,5-dicarboxylic acid 5-tert-butyl ester (F) were obtained in the form of a yellow oil which crystallised at RT.

Workup

  1. customThe solvent was removed under a vacuum
  2. dissolutionthe residue redissolved in a mixture of water/citric acid (pH=4) and ether
  3. customThe organic phase was separated off
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was removed under a vacuum

Sources & evidence

ORD record
ord-4b028e7fc28b4323bf74e2fb9113f99c
Source dataset
uspto-grants-2011_11
Patent number
US08048879B2

Reaction notes

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