Chlorotrimethylsilane → 1-(8-Methyl-8-azabicyclo[3.2.1]oct-2-en-2-yl)ethan-1-one

HRID 2226155노트

반응식

HRID 2226155 반응식
[C@@H:1]12[N:8]([CH3:9])[C@@H:5]([CH2:6][CH2:7]1)[CH2:4][CH:3]=[C:2]2[C:10]([O:12]CC)=O.[Si](Cl)(C)(C)[CH3:16].[Li]C>C1COCC1>[CH3:9][N:8]1[CH:5]2[CH2:6][CH2:7][CH:1]1[C:2]([C:10](=[O:12])[CH3:16])=[CH:3][CH2:4]2

참가 물질

5

반응물 3

HCID 6397ChlorotrimethylsilaneHCID 25222744Ecgonidine ethyl esterHCID 178418348HCID 178418348, 화합물

생성물 1

HCID 5857561-(8-Methyl-8-azabicyclo[3.2.1]oct-2-en-2-yl)ethan-1-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-100 °C

실험 절차

To a mixture of ethyl trop-2-ene-2-carboxylate (3.43 g, 0.019 mol) and Me3SiCl (10.32 g, 0.095 mol) in THF (70 mL) cooled to -100° C., MeLi (1.4 M, 17.07 n%L, 0.0239 mol) was added dropwise. After warming up to room temperature, the reaction mixture was stirred for 16 hours. Excess Me3SiCl and THF was evaporated off and the resulting residue was stirred with EtOH (6 mL) followed by water (6 mL). The mixture was then made acidic (6N HCl )and extracted with ether. The aqueous layer was made basic (solid K2CO3)and extracted with chloroform, dried (K2CO3) and concentrated to give

후처리

  1. temperatureAfter warming up to room temperature
  2. customExcess Me3SiCl and THF was evaporated off
  3. stirringthe resulting residue was stirred with EtOH (6 mL)
  4. extractionmade acidic (6N HCl )and extracted with ether
  5. extractionextracted with chloroform
  6. dry with materialdried (K2CO3)
  7. concentrationconcentrated
  8. customto give

출처 및 근거

ORD 기록
ord-ae26fdafb80b4b869101bcd29f8dbee7
출처 데이터셋
uspto-grants-1994_09
특허 번호
US05346911

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