Methanol → 6-Cyclobutylmethoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid

HRID 639301Notes

Reaction equation

HRID 639301 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:12]=[N:11][C:10]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[C:9]([O:18][CH2:19][CH:20]2[CH2:23][CH2:22][CH2:21]2)[N:8]=1)=[O:6].CO>O1CCCC1>[CH:20]1([CH2:19][O:18][C:9]2[N:8]=[C:7]([C:5]([OH:6])=[O:4])[CH:12]=[N:11][C:10]=2[N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 685689986-Cyclobutylmethoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid methyl ester

Product 1

HCID 685696866-Cyclobutylmethoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acidYield 80.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide 2M (10 mL) was added to a solution of the 6-cyclobutylmethoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid methyl ester (2.2 g, 7.4 mmol) in a (1:1) mixture of methanol and tetrahydrofuran (30 mL), the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated in vacuo and the residue was dissolved in ether (30 mL) and extracted with water (50 mL), the aqueous layer was washed with ether (2×50 mL) until only product remained in the aqueous layer. The aqueous layer was cooled to 0° C. and acidified with concentrated hydrochloric acid until precipitation was observed. The precipitate was filtered and dried in vacuo to afford 6-cyclobutylmethoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid as a cream solid 1.65 g (80% yield) LC@215 nm; Rt 1.98: 93%, m/z (ES+): 278 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ether (30 mL)
  3. extractionextracted with water (50 mL)
  4. washthe aqueous layer was washed with ether (2×50 mL) until only product
  5. temperatureThe aqueous layer was cooled to 0° C.
  6. customacidified with concentrated hydrochloric acid until precipitation
  7. filtrationThe precipitate was filtered
  8. customdried in vacuo

Sources & evidence

ORD record
ord-a189a0514ec04cceaadc5c432132002e
Source dataset
uspto-grants-2010_04
Patent number
US07691863B2

Reaction notes

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