Dimethylformamide → Methyl 1-benzyl-4-(3-hydroxy-1-propin-1-yl)-1,2,5,6-tetrahydropyridine-3-carboxylate

HRID 39713

反応式

HRID 39713 の反応式
CN(C)C=O.[CH2:6]([N:13]1[CH2:18][CH2:17][C:16](OS(C(F)(F)F)(=O)=O)=[C:15]([C:27]([O:29][CH3:30])=[O:28])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH:31](=[O:34])[C:32]#[CH:33].C(N(CC)C(C)C)(C)C>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C.O>[CH2:6]([N:13]1[CH2:18][CH2:17][C:16]([C:33]#[C:32][CH2:31][OH:34])=[C:15]([C:27]([O:29][CH3:30])=[O:28])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

参加物

9

反応物 4

HCID 6228DimethylformamideHCID 12222PropynalHCID 81531DiisopropylethylamineHCID 58912995Methyl 1-benzyl-4-(((trifluoromethyl)sulfonyl)oxy)-1,2,5,6-tetrahydropyridine-3-carboxylate

生成物 1

HCID 59398219Methyl 1-benzyl-4-(3-hydroxy-1-propin-1-yl)-1,2,5,6-tetrahydropyridine-3-carboxylate

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To 13 mL of an N,N-dimethylformamide solution containing 3.6 g of methyl 1-benzyl-4-(((trifluoromethyl)sulfonyl)oxy)-1,2,5,6-tetrahydropyridine-3-carboxylate, 0.75 mL of 2-propine-1-al and 2.2 mL of N,N-diisopropylethylamine, 61 mg of copper(I) iodide, and 0.14 g of bis(triphenylphosphine)palladium(II) dichloride were added under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 30 minutes. Water and ethyl acetate were added thereto. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform] to obtain 2.7 g of a brown oily substance, methyl 1-benzyl-4-(3-hydroxy-1-propin-1-yl)-1,2,5,6-tetrahydropyridine-3-carboxylate containing N,N-dimethylformamide.

後処理

  1. additionwere added under a nitrogen atmosphere
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washthe resultant solution was washed with an aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel column chromatography [eluent; chloroform]

出典と根拠

ORDレコード
ord-58d23a4911a44063b7220247b53800ea
出典データセット
uspto-grants-2013_09
特許番号
US08524738B2

関連ノート

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