Iodine → cis Ethyl 3-bromo-2-oxo-1-azacyclodecane-10-carboxylate

HRID 21963

반응식

HRID 21963 반응식
[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:3]1.P(Cl)(Cl)(Cl)(Cl)Cl.II.[Br:25]Br>C(Cl)Cl>[Br:25][C@H:11]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C@@H:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:3][C:2]1=[O:1]

참가 물질

6

반응물 4

HCID 807IodineHCID 24408BromineHCID 24819Phosphorus pentachlorideHCID 19930826Ethyl 2-oxo-1-azacyclodecane-10-carboxylate

생성물 1

HCID 131718120cis Ethyl 3-bromo-2-oxo-1-azacyclodecane-10-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

Ethyl 2-oxo-1-azacyclodecane-10-carboxylate (4.0 g, 17.6 mmol) is dissolved in methylene chloride (50 mL), and cooled to 0° C. Phosphorus pentachloride (3.85 g, 18.5 mmol) and iodine (0.051 g, 0.2 mmol) are added. The reaction is stirred for 15 minutes at 0° C. Then, bromine (3.10 g, 19.4 mmol) is added, and the reaction is stirred at 0° C. for 4 hours. The reaction is quenched by adding saturated sodium sulfite (until the color of excess bromine disappears), and extracted several times with methylene chloride. The combined organic layers are dried (Na2SO4), and the solvent is evaporated. The product is purified by silica gel chromatography (15% ethyl acetate/hexane) to give cis ethyl 3-bromo-2-oxo-1-azacyclodecane-10-carboxylate, m.p. 132°-134° C.

후처리

  1. stirringthe reaction is stirred at 0° C. for 4 hours
  2. customThe reaction is quenched
  3. additionby adding saturated sodium sulfite (until the color of excess bromine
  4. extractionextracted several times with methylene chloride
  5. dry with materialThe combined organic layers are dried (Na2SO4)
  6. customthe solvent is evaporated
  7. customThe product is purified by silica gel chromatography (15% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-ae6e3feffc3748f18ceeb2c6741450df
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05426103

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