Toluene → ethyl (2E)-3-(2-{[(tert-butoxycarbonyl)amino]methyl}phenyl)acrylate

HRID 64417ノート

反応式

HRID 64417 の反応式
Br[C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].CC1(C)C(C)(C)OB(/[CH:25]=[CH:26]/[C:27]([O:29][CH2:30][CH3:31])=[O:28])O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOCC>[C:8]([O:7][C:6]([NH:5][CH2:4][C:3]1[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=1/[CH:25]=[CH:26]/[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:12])([CH3:11])([CH3:10])[CH3:9]

参加物

7

反応物 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 70183002-Bromo-N-(tert-butoxycarbonyl)benzylamineHCID 23553751(E)-Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate

生成物 1

HCID 86713427ethyl (2E)-3-(2-{[(tert-butoxycarbonyl)amino]methyl}phenyl)acrylate収率 38.6%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 3283Diethyl Ether溶媒

反応条件

温度
100 °C

実験手順

A mixture of 1 g of tert-butyl (2-bromobenzyl)carbamate, 1.12 g of ethyl (2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate, 16 mg of palladium acetate, 72 mg of dicyclohexyl(2′,6′-dimethoxybiophenyl-2-yl)phosphine, 1.5 g of potassium phosphate, and 20 mL of toluene was stirred at 100° C. for 5 days. To the reaction mixture was added ether, followed by filtration through silica gel. The filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography to obtain 412 mg of ethyl (2E)-3-(2-{[(tert-butoxycarbonyl)amino]methyl}phenyl)acrylate.

後処理

  1. filtrationfollowed by filtration through silica gel
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-52bab543b59d45a5b32662ed568d4b3a
出典データセット
uspto-grants-2016_09
特許番号
US09447090B2

反応ノート

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