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

HRID 627245노트

반응식

HRID 627245 반응식
[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]

참가 물질

4

반응물 1

HCID 89852294(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-cyclopropylbut-3-en-2-ylcarbamate2회

생성물 1

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

시약·촉매·용매 2

HCID 10421208Zinc bromide촉매2회HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-dfe8c30f604f4108b5903b45896d8c99
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309245B2

반응 노트

불러오는 중…