Lithium Hydroxide → HCID 68566019, compound

HRID 639306Notes

Reaction equation

HRID 639306 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]([O:16][CH2:17][CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[N:6]=1)=[O:4].[OH-].[Li+]>O1CCCC1.CO.O>[CH:18]1([CH2:17][O:16][C:7]2[N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=[N:9][C:8]=2[N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 68565220HCID 68565220, compound

Product 1

HCID 68566019HCID 68566019, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.423 g (0.0014 mol) 6-cyclopentylmethoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid methyl ester in 5.5 mL tetrahydrofuran, 1.40 mL methanol and 1.4 mL water was added 2.8 mL of a 1M solution of lithium hydroxide in water and the mixture was stirred at room temperature for 4 h. The reaction mixture was partitioned between 10% aqueous citric acid and ethyl acetate. The phases were separated and the organic phase was washed with water (2×) and brine, dried over sodium sulfate and evaporated to yield 0.396 g (0.0014 mol) of the title compound as white crystals melting at 204-206° C.

Workup

  1. customThe reaction mixture was partitioned between 10% aqueous citric acid and ethyl acetate
  2. customThe phases were separated
  3. washthe organic phase was washed with water (2×) and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-4072d2a66b4641cd8a3a49e1ec4eb39b
Source dataset
uspto-grants-2010_04
Patent number
US07691863B2

Reaction notes

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