Benzyl chloroformate → Benzyl but-3-en-1-ylcarbamate

HRID 595228노트

반응식

HRID 595228 반응식
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[CH2:12]([NH2:16])[CH2:13][CH:14]=[CH2:15].C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[CH2:12]([NH:16][C:2](=[O:3])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:13][CH:14]=[CH2:15]

참가 물질

6

반응물 3

HCID 10387Benzyl chloroformateHCID 4437323-Buten-1-amineHCID 516892Sodium Bicarbonate

생성물 1

HCID 14688338Benzyl but-3-en-1-ylcarbamate

시약·촉매·용매 2

HCID 962Water용매2회HCID 6344Dichloromethane용매

실험 절차

Benzyl chloroformate (38 g, 0.22 mol) was added at 0° C. over 15 minutes to a mixture of but-3-en-1-amine (10 g, 0.14 mol) and sodium bicarbonate (35 g, 0.52 mol) in DCM (500 mL) and water (40 mL). The mixture was diluted with water and extracted with DCM. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether/EtOAc) to afford benzyl but-3-en-1-ylcarbamate. MS ESI calc'd. for C12H16NO2 [M+H]+ 206. found 206. 1H NMR (400 MHz, CDCl3) δ 7.36-7.30 (m, 5H), 5.80-5.70 (m, 1H), 5.11-5.01 (m, 4H), 3.79-3.25 (m, 2H), 2.29-2.24 (m, 2H).

후처리

  1. extractionextracted with DCM
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (petroleum ether/EtOAc)

출처 및 근거

ORD 기록
ord-5042bb1e9a8e480c97a726d774621ea3
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242984B2

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