Sodium triacetoxyborohydride → HCID 22247889, compound

HRID 890111Notes

Reaction equation

HRID 890111 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([C:12]1([CH3:18])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:11].[C:19]([O:23][C:24]1[C:25]([CH:30]=O)=[N:26][CH:27]=[CH:28][N:29]=1)([CH3:22])([CH3:21])[CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[C:19]([O:23][C:24]1[C:25]([CH2:30][N:15]2[CH2:14][CH2:13][C:12]([C:10](=[O:11])[CH2:9][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[F:2])([CH3:18])[CH2:17][CH2:16]2)=[N:26][CH:27]=[CH:28][N:29]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

7

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 22248122HCID 22248122, compoundHCID 222482803-(tert-Butoxy)pyrazine-2-carbaldehyde

Product 1

HCID 22247889HCID 22247889, compoundYield 72.9%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

After suspending 126 mg of 2-(2-fluorophenyl)-1-(4-methylpiperidin-4-yl)ethanone hydrochloride in 3 ml of dichloromethane, 100 mg of 3-tert-butoxypyrazine-2-carboxaldehyde and 146 mg of sodium triacetoxyborohydride were added and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, saturated aqueous sodium bicarbonate solution was added and extraction was performed with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (135 mg, 69% yield).

Workup

  1. additionwere added
  2. additionwas added
  3. extractionextraction
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c075ca2b72d5484a81e34d69109834cd
Source dataset
uspto-grants-2006_02
Patent number
US06995144B2

Reaction notes

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