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

HRID 336541ノート

反応式

HRID 336541 の反応式
[Cl:1][C:2]([Cl:7])(Cl)[C:3](Cl)=[O:4].[CH2:8]=[C:9]1[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10]1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.CCOCC>[Cl:1][C:2]1([Cl:7])[C:3](=[O:4])[CH2:8][C:9]21[CH2:10][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:12]2

参加物

6

反応物 3

HCID 6420Trichloroacetyl chlorideHCID 10340Sodium CarbonateHCID 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 3283Diethyl Ether溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

28.42 mL (254.65 mmol) of trichloroacetyl chloride dissolved in 70 mL of dimethoxyethane are added dropwise, at 0° C., to a mixture containing 7.98 g (47.16 mol) of tert-butyl 3-methyleneazetidine-1-carboxylate (WO 2008/124 085) and 36.48 g (282.94 mmol) of zinc-copper amalgam suspended in 200 mL of ether. The reaction medium is stirred at room temperature for 12 hours. The mixture is then poured portionwise into a sodium carbonate solution at 0° C. The solution obtained is filtered through Celite and rinsed thoroughly with water and ether. The aqueous phase is then separated out and extracted several times with ether. The combined organic phases are dried over sodium sulfate and the filtrate is concentrated under reduced pressure. After evaporating off the solvent, the product obtained, in the form of a brown oil, is used without further purification in the following step.

後処理

  1. additionare added dropwise, at 0° C., to a mixture
  2. customThe solution obtained
  3. filtrationis filtered through Celite
  4. washrinsed thoroughly with water and ether
  5. customThe aqueous phase is then separated out
  6. extractionextracted several times with ether
  7. dry with materialThe combined organic phases are dried over sodium sulfate
  8. concentrationthe filtrate is concentrated under reduced pressure
  9. customAfter evaporating off the solvent
  10. customthe product obtained, in the form of a brown oil
  11. customis used without further purification in the following step

出典と根拠

ORDレコード
ord-78a234039c404837bb6febdae6021911
出典データセット
uspto-grants-2014_11
特許番号
US08889702B2

反応ノート

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