Diethyl Ether → N-Boc-1-amino-1-(2,2,5,5-tetramethyl-1-cyclopentyl)ethenylcyclopropane

HRID 1906646

반응식

HRID 1906646 반응식
[CH3:1][C:2]1([CH3:11])[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[CH:3]1[CH2:9]Br.[Mg].[C:13]([NH:20][C:21]1(C=O)[CH2:23][CH2:22]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[CH3:26]COCC>>[C:13]([NH:20][C:21]1([C:9]([CH:3]2[C:2]([CH3:11])([CH3:1])[CH2:6][CH2:5][C:4]2([CH3:8])[CH3:7])=[CH2:26])[CH2:23][CH2:22]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

참가 물질

5

반응물 4

HCID 3283Diethyl EtherHCID 5462224Magnesium2회HCID 10352385(1-Formylcyclopropyl)carbamic acid tert-butyl esterHCID 136292612,2,5,5-Tetramethyl-1-cyclopentylmethylbromide

생성물 1

HCID 70445455N-Boc-1-amino-1-(2,2,5,5-tetramethyl-1-cyclopentyl)ethenylcyclopropane

실험 절차

A solution of 2,2,5,5-Tetramethyl-1-cyclopentylmethyl bromide in ether is added slowly to magnesium turnings until the Grignard reagent begins to form. The remainder of the alkyl bromide is then added and the mixture is stirred until all the magnesium dissolves. At 0° C. a solution of N-Boc-1-amino-1-cyclopropanecarboxaldehyde is then added and the mixture is stirred overnight. The reaction is quenched with 1M HCl, extracted with ether and the extracts are evaporated. The residue is dissolved in dioxane and 2M H2SO4 is added. The mixture is heated until the alcohol is dehydrated, as shown by thin layer chromatography. Water is added and the mixture is extracted with ether. The organic layer is dried over MgSO4 and evaporated to give N-Boc-1-amino-1-(2,2,5,5-tetramethyl-1-cyclopentyl)ethenylcyclopropane.

후처리

  1. customto form
  2. dissolutiondissolves
  3. customThe reaction is quenched with 1M HCl
  4. extractionextracted with ether
  5. customthe extracts are evaporated
  6. dissolutionThe residue is dissolved in dioxane
  7. addition2M H2SO4 is added
  8. temperatureThe mixture is heated until the alcohol
  9. additionWater is added
  10. extractionthe mixture is extracted with ether
  11. dry with materialThe organic layer is dried over MgSO4
  12. customevaporated

출처 및 근거

ORD 기록
ord-ece9711cc1f44f13aa70f9978ce5cf48
출처 데이터셋
uspto-grants-1987_03
특허 번호
US04652676

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