Tert-butyl 4-(6-{2-[4-(hydroxymethyl)phenyl]vinyl}pyridin-3-yl)piperazine-1-carboxylate → Tert-butyl 4-(6-{2-[4-(hydroxymethyl)phenyl]ethyl}pyridin-3-yl)piperazine-1-carboxylate

HRID 1465472ノート

反応式

HRID 1465472 の反応式
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]2[N:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)=[CH:5][CH:4]=1>C(OCC)(=O)C.[C].[Pd]>[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)=[CH:5][CH:4]=1

参加物

4

反応物 1

HCID 67030232Tert-butyl 4-(6-{2-[4-(hydroxymethyl)phenyl]vinyl}pyridin-3-yl)piperazine-1-carboxylate

生成物 1

HCID 67030135Tert-butyl 4-(6-{2-[4-(hydroxymethyl)phenyl]ethyl}pyridin-3-yl)piperazine-1-carboxylate収率 84.1%

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of tert-butyl 4-(6-{2-[4-(hydroxymethyl)phenyl]vinyl}pyridin-3-yl)piperazine-1-carboxylate (848.0 mg, 2.144 mmol) in ethyl acetate (45 ml) was added 5% palladium carbon (84.5 mg, 50% containing water), and the mixture was hydrogenated at room temperature, under atmospheric pressure for 11 hrs. The reaction mixture was filtered through Celite. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=6:4→7:3) to give tert-butyl 4-(6-{2-[4-(hydroxymethyl)phenyl]ethyl}pyridin-3-yl)piperazine-1-carboxylate (716.9 mg, yield 84.1%) as a white solid.

後処理

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=6:4→7:3)

出典と根拠

ORDレコード
ord-7f98ae0a48524e549174f13142cf7a81
出典データセット
uspto-grants-2015_04
特許番号
US08999989B2

反応ノート

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