Sodium Bicarbonate → HCID 86648982, compound

HRID 1877815Notes

Reaction equation

HRID 1877815 reaction equation
[Cl:1][C:2]1[C:3]([CH:9]=O)=[N:4][CH:5]=[C:6]([Cl:8])[N:7]=1.[CH2:11]([NH:18][CH2:19][C@@H:20]([OH:22])[CH3:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C1COCC1.C(OCC)(=O)C.C(O)(=O)C>[CH2:11]([N:18]([CH2:9][C:3]1[C:2]([Cl:1])=[N:7][C:6]([Cl:8])=[CH:5][N:4]=1)[CH2:19][C@@H:20]([OH:22])[CH3:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 964914HCID 964914, compoundHCID 5049666Sodium triacetoxyborohydrideHCID 156968403,5-Dichloropyrazine-2-carbaldehyde

Product 1

HCID 86648982HCID 86648982, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3,5-dichloropyrazine-2-carbaldehyde (3.0 g), (2S)-1-(benzylamino)propan-2-ol (3.36 g) and acetic acid (4.9 mL) in THF (50 mL) was added sodium triacetoxyborohydride (7.18 g), and the mixture was stirred at room temperature overnight. The reaction solution was diluted with ethyl acetate, and basified with saturated aqueous sodium hydrogen carbonate. The organic layer was separated, washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (solvent gradient: 5→25% ethyl acetate/hexane) to give the title compound (3.48 g, 63%) as a pale-yellow oil.

Workup

  1. customThe organic layer was separated
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by basic silica gel column chromatography (solvent gradient: 5→25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b63d603c123f4f8497d6b63217a44b99
Source dataset
uspto-grants-2012_11
Patent number
US08314088B2

Reaction notes

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