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

HRID 21966

반응식

HRID 21966 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-bc023ee232b849a4ba76f663d1c2ba20
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05426103

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