Bromine → 6-(Bromomethyl)-1,3-oxazinan-2-one

HRID 595229노트

반응식

HRID 595229 반응식
[Br:1]Br.[CH2:3]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1C=CC=CC=1)[CH2:4]C=C>C(Cl)Cl.O>[Br:1][CH2:11][CH:10]1[O:9][C:8](=[O:17])[NH:7][CH2:3][CH2:4]1

참가 물질

5

반응물 2

HCID 24408BromineHCID 14688338Benzyl but-3-en-1-ylcarbamate

생성물 1

HCID 1182088706-(Bromomethyl)-1,3-oxazinan-2-one

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

Bromine (11 g, 68 mmol) was added to a mixture of benzyl but-3-en-1-ylcarbamate (7 g, 34 mmol) in DCM at room temperature under N2. The mixture was stirred at room temperature for 4 hours. 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 6-(bromomethyl)-1,3-oxazinan-2-one. 1H NMR (400 MHz, CDCl3) δ 6.14 (s, 1H), 4.49-4.45 (m, 1H), 3.59-3.56 (m, 1H), 3.46-3.39 (m, 3H), 2.24-2.20 (m, 1H), 1.95-1.89 (m, 1H).

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-69dfa9a436d94c1cb098a91b0bcfacb6
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242984B2

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