Piperidine → 5-Piperidin-1-ylmethyl-pyrazine-2-carboxylic acid methyl ester

HRID 30481Notes

Reaction equation

HRID 30481 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([CH:11]=O)=[CH:7][N:6]=1)=[O:4].[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([CH2:11][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:7][N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 44515461Methyl 5-formylpyrazine-2-carboxylate

Product 1

HCID 445157725-Piperidin-1-ylmethyl-pyrazine-2-carboxylic acid methyl esterYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-formyl-pyrazine-2-carboxylic acid methyl ester (0.400 g, 2.40 mmol), piperidine (0.204 g, 2.40 mmol), and NaB(OAc)3H (1.40 g, 3.60 mmol) in DCM (10 mL) was stirred for 18 h at rt. The reaction was quenched by the addition of 10% aq. NaOH (10 mL) and the mixture was stirred for 30 min. The mixture was extracted with DCM (3×20 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated to yield the title compound (0.130 g, 23%).

Workup

  1. customThe reaction was quenched by the addition of 10% aq. NaOH (10 mL)
  2. stirringthe mixture was stirred for 30 min
  3. extractionThe mixture was extracted with DCM (3×20 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3f12238eb5cc4ed5844e429ed7bc5b18
Source dataset
uspto-grants-2008_09
Patent number
US07423147B2

Reaction notes

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