Lithium Hydroxide → HCID 67505404, compound

HRID 1159220Notes

Reaction equation

HRID 1159220 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-87b6718c47944f049cf4c95ae27e2416
Source dataset
uspto-grants-2010_10
Patent number
US07812028B2

Reaction notes

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