Water → (5-Tert-butyl-pyridin-2-ylmethyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amine

HRID 2243189ノート

反応式

HRID 2243189 の反応式
[H-].C([Al+]CC(C)C)C(C)C.[Cl:11][C:12]1[CH:13]=[C:14]([CH2:19][CH2:20][NH:21][C:22]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][N:25]=2)=O)[CH:15]=[CH:16][C:17]=1[Cl:18].O>C1COCC1>[C:30]([C:27]1[CH:28]=[CH:29][C:24]([CH2:22][NH:21][CH2:20][CH2:19][C:14]2[CH:15]=[CH:16][C:17]([Cl:18])=[C:12]([Cl:11])[CH:13]=2)=[N:25][CH:26]=1)([CH3:33])([CH3:31])[CH3:32]

参加物

5

反応物 3

HCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 670177025-Tert-butyl-pyridine-2-carboxylic acid [2-(3,4-dichloro-phenyl)-ethyl]-amide

生成物 1

HCID 67017705(5-Tert-butyl-pyridin-2-ylmethyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amine収率 68.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Diisobutylaluminum hydride (1 M solution in THF, 0.40 mL, 0.40 mmol) was added dropwise to a solution of 5-tert-butyl-pyridine-2-carboxylic acid [2-(3,4-dichloro-phenyl)-ethyl]-amide (195 mg, 0.555 mmol) in THF (2 mL) at 0° C., then after 15 min, the reaction was stopped by careful addition of water. The reaction mixture was partitioned between ethyl acetate and 1 M aq. potassium sodium tartrate solution, the organic layer was washed with brine, dried (MgSO4), and concentrated. Chromatography (SiO2, heptane/ethyl acetate 1:1, then dichloromethane/methanol 9:1) afforded (5-tert-butyl-pyridin-2-ylmethyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amine (128 mg, 68%). Yellow oil, MS (ISP): 337.3 (M+H)+.

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate and 1 M aq. potassium sodium tartrate solution
  2. washthe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-4ba12d7ee28f444ebd704625a3130b46
出典データセット
uspto-grants-2010_03
特許番号
US07674815B2

反応ノート

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