Trichloroacetyl chloride → tert-Butyl 5,5-dichloro-6-oxo-2-azaspiro[3.3]heptane-2-carboxylate

HRID 1943595ノート

反応式

HRID 1943595 の反応式
[CH2:1]=[C:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.[Cl:13][C:14]([Cl:19])(Cl)[C:15](Cl)=[O:16].COCCOC>C(OCC)C.[Zn]>[Cl:13][C:14]1([Cl:19])[C:15](=[O:16])[CH2:1][C:2]21[CH2:3][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:5]2

参加物

6

反応物 3

HCID 6420Trichloroacetyl chlorideHCID 80711,2-DimethoxyethaneHCID 55269097tert-Butyl 3-methylideneazetidine-1-carboxylate

生成物 1

HCID 69669942tert-Butyl 5,5-dichloro-6-oxo-2-azaspiro[3.3]heptane-2-carboxylate

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 3283Diethyl Ether溶媒

反応条件

温度
10 °C

実験手順

Under an inert atmosphere, 7.728 g (118.19 mmoles) of zinc in nanopowder form are suspended in 100 ml of diethyl ether. 5.00 g (29.55 mmoles) of tert-butyl 3-methylene-azetidine-1-carboxylate (WO 2008124085) are added, then the medium is cooled to 10° C. A solution of 6.60 ml (59.09 mmoles) of trichloroacetyl chloride in ml of 1,2-dimethoxyethane is added drop by drop while maintaining the temperature of the reaction medium between 26 and 30° C. After stirring for 14 hrs at ambient temperature, the medium is filtered over celite, the celite is copiously rinsed with diethyl ether and the filtrate is partially concentrated under reduced pressure. The crude reaction product thus obtained is used as such in the following stage.

後処理

  1. temperaturewhile maintaining the temperature of the reaction medium between 26 and 30° C
  2. filtrationthe medium is filtered over celite
  3. washthe celite is copiously rinsed with diethyl ether
  4. concentrationthe filtrate is partially concentrated under reduced pressure
  5. customThe crude reaction product
  6. customthus obtained

出典と根拠

ORDレコード
ord-ade1e48e085e4c8d910f142994fe43b5
出典データセット
uspto-grants-2013_03
特許番号
US08394787B2

反応ノート

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