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

HRID 1888171Notes

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

Participants

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

temperatureThe solution was cooled to room temperature
concentrationconcentrated
customto remove organic solvents
concentrationThe mixture was concentrated to dryness under vacuum
customazeotroping with toluene (2×20 mL)
customwas removed
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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