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

HRID 2226155ノート

反応式

HRID 2226155 の反応式
[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

参加物

5

反応物 3

HCID 6397ChlorotrimethylsilaneHCID 25222744Ecgonidine ethyl esterHCID 178418348HCID 178418348、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-100 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-ae26fdafb80b4b869101bcd29f8dbee7
出典データセット
uspto-grants-1994_09
特許番号
US05346911

反応ノート

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