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

HRID 1794136노트

반응식

HRID 1794136 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-5159be1b9b1c4d23b8b8a21749887f32
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07022707B2

반응 노트

불러오는 중…