(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-cyclopropylbut-3-en-2-ylcarbamate → (S)-1-(tert-butyldimethylsilyloxy)-3-cyclopropylbut-3-en-2-amine

HRID 627245ノート

反応式

HRID 627245 の反応式
[Si:1]([O:8][CH2:9][C@@H:10]([NH:16]C(=O)OC(C)(C)C)[C:11]([CH:13]1[CH2:15][CH2:14]1)=[CH2:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(Cl)Cl.[Br-].[Zn+2].[Br-]>[Si:1]([O:8][CH2:9][C@@H:10]([NH2:16])[C:11]([CH:13]1[CH2:15][CH2:14]1)=[CH2:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

4

反応物 1

HCID 89852294(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-cyclopropylbut-3-en-2-ylcarbamate2 回

生成物 1

HCID 89851324(S)-1-(tert-butyldimethylsilyloxy)-3-cyclopropylbut-3-en-2-amine収率 96.3%

試薬・触媒・溶媒 2

HCID 10421208Zinc bromide触媒2 回HCID 6344Dichloromethane溶媒

実験手順

To a solution of (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-cyclopropylbut-3-en-2-ylcarbamate (Intermediate 233, 6.77 g, 19.82 mmol) in DCM (100 mL) at room temperature was added zinc bromide (17.86 g, 79.28 mmol). The reaction mixture was stirred overnight at room temperature. Another 1 eq of zinc bromide was added. After several hours the reaction mixture was filtered and washed with saturated sodium bicarbonate. The resulting emulsion was filtered through a nylon filter and the layers were separated. The organics were dried over magnesium sulfate, filtered and concentrated to afford the title compound as a yellow oil (4.61 g, 96%).

後処理

  1. filtrationAfter several hours the reaction mixture was filtered
  2. washwashed with saturated sodium bicarbonate
  3. filtrationThe resulting emulsion was filtered through a nylon
  4. filtrationfilter
  5. customthe layers were separated
  6. dry with materialThe organics were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-dfe8c30f604f4108b5903b45896d8c99
出典データセット
uspto-grants-2016_04
特許番号
US09309245B2

反応ノート

読み込み中…