Sodium Hydroxide → HCID 22248055, compound

HRID 890076Notes

Reaction equation

HRID 890076 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1/[CH:7]=[CH:8]/[CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[CH3:15][O:16][C:17]1[C:18]([CH:23]=O)=[N:19][CH:20]=[CH:21][N:22]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>O1CCCC1>[CH3:15][O:16][C:17]1[C:18]([CH2:23][N:12]2[CH2:13][CH2:14][CH:9](/[CH:8]=[CH:7]/[C:3]3[S:4][CH:5]=[CH:6][C:2]=3[CH3:1])[CH2:10][CH2:11]2)=[N:19][CH:20]=[CH:21][N:22]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 158805973-Methoxypyrazine-2-carbaldehydeHCID 22248429HCID 22248429, compound

Product 1

HCID 22248055HCID 22248055, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After dissolving 139 mg of (E)-4-[2-(3-methyl-2-thienyl)vinyl]piperidine in 7 ml of tetrahydrofuran, 111 mg of 3-methoxypyrazine-2-carboxaldehyde and 213 mg of sodium triacetoxyborohydride were added while stirring, and the stirring was continued overnight at room temperature. A 1N sodium hydroxide solution was added to the reaction mixture to render it alkaline, and then extraction was performed with ethyl acetate. The extract 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 NH silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (120 mg, 54% yield).

Workup

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

Sources & evidence

ORD record
ord-e33a24c57d85442e85e5aae4b597e4d7
Source dataset
uspto-grants-2006_02
Patent number
US06995144B2

Reaction notes

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