Lithium Hydroxide → HCID 67505404, compound

HRID 1929824Notes

Reaction equation

HRID 1929824 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[N:6]=1)=[O:4].[OH-].[Li+]>O1CCCC1.O.CO>[Cl:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:7]1[N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=[N:9][C:8]=1[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 67504874HCID 67504874, compound

Product 1

HCID 67505404HCID 67505404, compoundYield 97.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(2-chloro-phenyl)-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid methyl ester (0.15 g) in tetrahydrofuran (2 mL), water (0.5 mL) and methanol (0.5 mL) was added at room temperature 1 ml of a 1M solution of lithium hydroxide in water and the mixture was stirred for 2 h. The resulting solution was partitioned between 10% aqueous citric acid and ethyl acetate. The phases were separated and the organic layer was washed with water and brine. The organic phase was dried over magnesium sulfate and evaporated to yield 0.14 g of the title compound as white solid, MS (ISP) 304.1 (M+H)+.

Workup

  1. customThe resulting solution was partitioned between 10% aqueous citric acid and ethyl acetate
  2. customThe phases were separated
  3. washthe organic layer was washed with water and brine
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-9699cee07ee745ec85a09b299d438f01
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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