Magnesium → N-Boc-2-amino-2-methyl-4-(2,2,5,5-tetramethyl-1-cyclopentyl)butene

HRID 256252

反応式

HRID 256252 の反応式
[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]([CH3:25])([CH3:24])[CH:22]=O)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>CCOCC>[C:13]([NH:20][C:21]([CH3:25])([CH:24]=[CH:9][CH:3]1[C:2]([CH3:11])([CH3:1])[CH2:6][CH2:5][C:4]1([CH3:8])[CH3:7])[CH3:22])([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14]

参加物

5

反応物 3

HCID 5462224Magnesium2 回HCID 136292612,2,5,5-Tetramethyl-1-cyclopentylmethylbromideHCID 14578674tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamate

生成物 1

HCID 70445521N-Boc-2-amino-2-methyl-4-(2,2,5,5-tetramethyl-1-cyclopentyl)butene

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

A solution of 2,2,5,5-Tetramethyl-1-cyclopentylmethyl bromide in ether is added slowly to magnesium turnings until the Grignard reagent beings to form. The remainder of the alkyl bromide is then added and the mixture is stirred until all of the magnesium has dissolved. At 0° C. a solution of N-Boc-2-amino-2-methylpropanal 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 dissolves 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 extracted with ether. The organic layer is dried over MgSO4 and evaporated to give N-Boc-2-amino-2-methyl-4-(2,2,5,5-tetramethyl-1-cyclopentyl)butene.

後処理

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

出典と根拠

ORDレコード
ord-80bc5b99725c46fcbfced3188e09e587
出典データセット
uspto-grants-1987_10
特許番号
US04701552

関連ノート

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