Pyridine → (R)-4-Chlorocarbonyl-3-ethyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 1794136ノート

反応式

HRID 1794136 の反応式
[Cl:1][C:2]([O:5]C(=O)OC(Cl)(Cl)Cl)(Cl)Cl.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][NH:23][C@H:22]([CH2:26][CH3:27])[CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].N1C=CC=CC=1>ClCCl>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][N:23]([C:2]([Cl:1])=[O:5])[C@H:22]([CH2:26][CH3:27])[CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

参加物

5

反応物 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 24820337(R)-1-Boc-3-Ethylpiperazine

生成物 1

HCID 86586001(R)-4-Chlorocarbonyl-3-ethyl-piperazine-1-carboxylic acid tert-butyl ester収率 262.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

Bis-(trichloromethyl)-carbonate (13.9 g, 47 mM) was dissolved in dichloromethane (500 mL) and cooled to 0° C. A mixture of (R)-3-ethyl-piperazine-1-carboxylic acid tert-butyl ester (26.5 g; 0.124 M) and pyridine (10.9 mL, 0.136 M) in dichloromethane (150 mL) was added dropwise with stirring (0–3° C.). Stirring was continued for another ½ h at room temperature. The mixture was washed with water and brine, the water phases were extracted with dichloromethane, organic phases were pooled, dried with Na2SO4 and evaporated to yield a brown oil (34 g, 99%) which crystallized upon standing; MS (EI): 276.2 (M)+.

後処理

  1. additionwas added dropwise
  2. stirringStirring
  3. washThe mixture was washed with water and brine
  4. extractionthe water phases were extracted with dichloromethane, organic phases
  5. dry with materialdried with Na2SO4
  6. customevaporated

出典と根拠

ORDレコード
ord-5159be1b9b1c4d23b8b8a21749887f32
出典データセット
uspto-grants-2006_04
特許番号
US07022707B2

反応ノート

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