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

HRID 5391

反応式

HRID 5391 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-506b9adb631a461cb9ffccba8d2f7bb0
出典データセット
uspto-grants-1993_09
特許番号
US05244889

関連ノート

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