Pyridine → N-[(1R)-1-(4-bromophenyl)ethyl]acetamide

HRID 858575

반응식

HRID 858575 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.[C:11](OC(=O)C)(=[O:13])[CH3:12].N1C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][C:11](=[O:13])[CH3:12])[CH3:9])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 853000(R)-4-bromo-alpha-methylbenzylamine

생성물 1

HCID 793485N-[(1R)-1-(4-bromophenyl)ethyl]acetamide수율 100%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
25 °C

실험 절차

To a stirred solution of (R)-(+)-1-(4-bromophenyl)ethylamine (0.52 g, 2.59 mmol) in anhydrous CH2Cl2 (5 mL) under argon were added acetic anhydride (0.37 mL, 3.89 mmol) and Pyridine (0.31 mL, 3.89 mmol). The resulting solution was stirred at 25° C. for 3 hrs. The reaction mixture was quenched with saturated 1 N HCl and extracted with EtOAc (30 mL). The organic phase was washed with brine (50 mL), dried over Na2SO4 and evaporated. The residue was purified by flash column chromatography (80% EtOAc in hexanes) to give the product (0.62 g, 100%) as a white solid.

후처리

  1. customThe reaction mixture was quenched with saturated 1 N HCl
  2. extractionextracted with EtOAc (30 mL)
  3. washThe organic phase was washed with brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by flash column chromatography (80% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-e11f93c270734f01918ae524961d5629
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07148226B2

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