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

HRID 1453025

반응식

HRID 1453025 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:11][S:12](Cl)(=[O:14])=[O:13].N1C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][S:12]([CH3:11])(=[O:14])=[O:13])[CH3:9])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 853000(R)-4-bromo-alpha-methylbenzylamine

생성물 1

HCID 28560458N-[(1R)-1-(4-bromophenyl)ethyl]methanesulfonamide수율 58%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
25 °C

실험 절차

To a stirred solution of (R)-(+)-1-(4-bromophenyl)ethylamine (0.5 g, 2.49 mmol), in anhydrous CH2Cl2 (5 mL) under argon were added methane sulfonyl chloride (0.23 mL, 2.99 mmol) and Pyridine (0.30 mL, 3.73 mmol). The resulting solution was stirred at 25° C. for 3 hrs. The reaction mixture was quenched with 1N 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 (0.40 g, 58%) as a white solid. 1H NMR (CDCl3) δ: 1.52 (d, J=6.8 Hz, 3H), 2.67 (s, 3H), 4.61-4.72 (m, 2H), 7.24 (d, J=8.3 Hz, 2H), 7.51 (d, J=8.3 Hz, 2H). ESIMS (MNa+): 279.

후처리

  1. customThe reaction mixture was quenched with 1N 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-35a6a1af5a1e4ed185a99768c09f9685
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07473790B2

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