Stannous Chloride → tert-Butyl 1-(3-amino-4-chlorobenzyl)-2,2-difluorocyclopropanecarboxylate

HRID 1475628노트

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HRID 1475628 반응식
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][C:7]2([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9][C:8]2([F:11])[F:10])=[CH:4][C:3]=1[N+:21]([O-])=O.[Sn](Cl)Cl.[F-].[K+]>O1CCOCC1.Cl>[NH2:21][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:2]=1[Cl:1])[CH2:6][C:7]1([C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])[CH2:9][C:8]1([F:11])[F:10]

참가 물질

6

반응물 3

HCID 24479Stannous ChlorideHCID 522689Potassium FluorideHCID 68170286(+/-)-Tert-butyl 1-(4-chloro-3-nitrobenzyl)-2,2-difluorocyclopropane-carboxylate

생성물 1

HCID 68170287tert-Butyl 1-(3-amino-4-chlorobenzyl)-2,2-difluorocyclopropanecarboxylate

시약·촉매·용매 2

HCID 313Hydrochloric Acid촉매HCID 312751,4-Dioxane용매

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온도
70 °C

실험 절차

1.60 g (4.60 mmol) of (+/−)-tert-butyl 1-(4-chloro-3-nitrobenzyl)-2,2-difluorocyclopropanecarboxylate were dissolved in 20 ml of dioxane, and 4.36 g (23.0 mmol) of tin(II) chloride and a few drops of 1 N hydrochloric acid were added at RT. The reaction mixture was heated at 70° C. for 1 h. After cooling to RT, 10 ml of 10% strength aqueous potassium fluoride solution were added. The mixture was extracted three times with ethyl acetate, and the combined organic phases were dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 50:1→10:1). This gave 1.16 g of the target product (79.3% of theory).

후처리

  1. temperatureAfter cooling to RT
  2. extractionThe mixture was extracted three times with ethyl acetate
  3. dry with materialthe combined organic phases were dried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 50:1→10:1)

출처 및 근거

ORD 기록
ord-1ffbbb596b87490384a5f5e0ee0c88eb
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018258B2

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