Diisobutylaluminumhydride → HCID 86679038, compound

HRID 1907871Notes

Reaction equation

HRID 1907871 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([NH:11][CH2:12][CH2:13][CH2:14][CH:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)=[CH:7][N:6]=1)=O.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[CH3:21][N:18]1[CH2:19][CH2:20][CH:15]([CH2:14][CH2:13][CH2:12][NH:11][C:8]2[N:9]=[CH:10][C:5]([CH:3]=[O:2])=[N:6][CH:7]=2)[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 68436940HCID 68436940, compound

Product 1

HCID 86679038HCID 86679038, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A −78° C. solution of 5-[3-(1-methyl-piperidin-4-yl)-propylamino]-pyrazine-2-carboxylic acid methyl ester in DCM (0.1 M) was treated with diisobutylaluminum hydride (1 M in hexanes; 1 equiv.) dropwise. The reaction was quenched with 1 M H2SO4, neutralized with satd. aq. NaHCO3, and diluted with MeOH, CHCl3, and satd. aq. sodium potassium tartrate. The mixture was stirred vigourously until the layers separated. The organic layer was dried (Na2SO4) and concentrated to give the crude product, which was used in the next step without further purification.

Workup

  1. customThe reaction was quenched with 1 M H2SO4
  2. additionaq. NaHCO3, and diluted with MeOH, CHCl3
  3. customseparated
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ee963dbd0d0d410cb9fc46e4b7864d5b
Source dataset
uspto-grants-2013_12
Patent number
US08598189B2

Reaction notes

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