Boron trifluoride etherate → Ethyl 3-methylidene-2-oxo-1-azacyclodecane-10-carboxylate

HRID 5394

反应方程式

HRID 5394 反应方程式
C[Si]([CH2:5][C:6]1(O)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:8][C:7]1=[O:21])(C)C.B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:5]=[C:6]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:8][C:7]1=[O:21]

参与物

4

反应物 2

HCID 8000Boron trifluoride etherateHCID 19930812Ethyl 3-(trimethylsilylmethyl)-3-hydroxy-2-oxo-1-azacyclodecane-10-carboxylate

产物 1

HCID 19930803Ethyl 3-methylidene-2-oxo-1-azacyclodecane-10-carboxylate

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

实验过程

Ethyl 3-(trimethylsilylmethyl)-3-hydroxy-2-oxo-1-azacyclodecane-10-carboxylate (0.98 g, 2.98 mmol) is dissolved in methylene chloride (50 mL), and boron trifluoride etherate (1.8 mL, 15 mmol) is added. The reaction is stirred at room temperature for 26 hours. The reaction is then quenched with saturated ammonium chloride and extracted several times with methylene chloride. The combined organic layers are dried (MgSO4), and the solvent is evaporated. The product is purified by silica gel chromatography (20% ethyl acetate/hexane) to give ethyl 3-methylidene-2-oxo-1-azacyclodecane-10-carboxylate, m.p. 91°-92° C.

后处理

  1. customThe reaction is then quenched with saturated ammonium chloride
  2. extractionextracted several times with methylene chloride
  3. dry with materialThe combined organic layers are dried (MgSO4)
  4. customthe solvent is evaporated
  5. customThe product is purified by silica gel chromatography (20% ethyl acetate/hexane)

来源与证据

ORD记录
ord-33f9adfd6f284316b20090b99cc163ce
来源数据集
uspto-grants-1993_09
专利号
US05244889

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