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Lithium Hydroxide → 3-methyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazole-7-carboxylic acid

HRID 1888171
Notes
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Reaction equation

HRID 1888171 reaction equation
[CH3:1][C:2]1[N:3]2[CH2:9][CH2:8][CH:7]([C:10]([O:12]CC)=[O:11])[C:4]2=[N:5][N:6]=1.[Li+].[OH-]>C1COCC1.O.CO>[CH3:1][C:2]1[N:3]2[CH2:9][CH2:8][CH:7]([C:10]([OH:12])=[O:11])[C:4]2=[N:5][N:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57907459ethyl 3-methyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazole-7-carboxylate

Product 1

HCID 579074853-methyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazole-7-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 3-methyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]-triazole-7-carboxylate (400 mg, 2.05 mmol) from step A in THF/water/MeOH was added LiOH (250 mg, 10.3 mmol) and the resulting solution was heated to 60° C. for 16 h. The solution was cooled to room temperature and concentrated to remove organic solvents. The aqueous layer was then acidified to pH of ˜5 using 2N HCl. The mixture was concentrated to dryness under vacuum, azeotroping with toluene (2×20 mL) to make sure all water was removed. The material was used without further purification with lithium chloride as a by-product. LC-MS: m/z (ES)=168 (MH)+.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. concentrationconcentrated
  3. customto remove organic solvents
  4. concentrationThe mixture was concentrated to dryness under vacuum
  5. customazeotroping with toluene (2×20 mL)
  6. customwas removed
  7. customThe material was used without further purification with lithium chloride as a by-product

Sources & evidence

ORD record
ord-43edc875574f40cf8fdc3c071751ec63
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08501786B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes