Methyl 3-bromoprop-2-ynoate → 7-Tert-butyl 2-methyl 3-bromo-7-azabicyclo[2.2.1]hepta-2,5-diene-2,7-dicarboxylate

HRID 81121

反応式

HRID 81121 の反応式
[Br:1][C:2]#[C:3][C:4]([O:6][CH3:7])=[O:5].[N:8]1([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9]1>>[Br:1][C:2]1[CH:9]2[N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:12]([CH:11]=[CH:10]2)[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

参加物

3

反応物 2

HCID 294619Methyl 3-bromoprop-2-ynoateHCID 643494tert-butyl 1H-pyrrole-1-carboxylate

生成物 1

HCID 152851047-Tert-butyl 2-methyl 3-bromo-7-azabicyclo[2.2.1]hepta-2,5-diene-2,7-dicarboxylate

反応条件

温度
95 °C

実験手順

Into a 2000-mL 3-necked round-bottom flask was placed methyl 3-bromopropiolate (120 g, 736.33 mmol, 1.00 equiv) and tert-butyl 1H-pyrrole-1-carboxylate (615.61 g, 3.68 mol, 5.00 equiv). The resulting solution was stirred for 30 hr at 95° C. in an oil bath. The reaction mixture was cooled and distilled under reduced pressure (20 mm Hg). The fraction collected at 55° C. was purified by silica gel chromatography (ethyl acetate/petroleum ether, 1:20) to afford 7-tert-butyl 2-methyl 3-bromo-7-azabicyclo[2.2.1]hepta-2,5-diene-2,7-dicarboxylate as a yellow liquid.

後処理

  1. customInto a 2000-mL 3-necked round-bottom flask was placed
  2. temperatureThe reaction mixture was cooled
  3. distillationdistilled under reduced pressure (20 mm Hg)
  4. customThe fraction collected at 55° C.
  5. customwas purified by silica gel chromatography (ethyl acetate/petroleum ether, 1:20)

出典と根拠

ORDレコード
ord-2df515ddc6034b79a504ec8fcf1ba9ea
出典データセット
uspto-grants-2014_09
特許番号
US08846657B2

関連ノート

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