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

HRID 1453025ノート

反応式

HRID 1453025 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-35a6a1af5a1e4ed185a99768c09f9685
出典データセット
uspto-grants-2009_01
特許番号
US07473790B2

反応ノート

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