Triethylamine → ((2R)-2-phenylpropyl)[(methylethyl)sulfonyl]amine

HRID 392936ノート

反応式

HRID 392936 の反応式
[C:1]1([C@@H:7]([CH3:10])[CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[CH:27]([S:30](Cl)(=[O:32])=[O:31])([CH3:29])[CH3:28]>CCCCCC.C(Cl)Cl>[C:1]1([C@@H:7]([CH3:10])[CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([C@@H:7]([CH3:10])[CH2:8][NH:9][S:30]([CH:27]([CH3:29])[CH3:28])(=[O:32])=[O:31])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 824082-Propanesulfonyl chlorideHCID 1547949(R)-(+)-beta-Methylphenethylamine

生成物 2

HCID 1547949(R)-(+)-beta-MethylphenethylamineHCID 11481889((2R)-2-phenylpropyl)[(methylethyl)sulfonyl]amine収率 180.3%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8058Hexane溶媒

実験手順

To a solution of the (2R)-2-phenylpropylamine (1.2 g, 8.87 mmol) in hexane (16.0 mL) was added triethylamine (2.47 mL, 17.74 mmol) and is dimethylaminopyridine (0.30 g, 2.47 mmol). Cooled reaction to 5° C., then added a solution of isopropylsulfonyl chloride (0.97 mL, 8.69 mmol) dissolved in methylene chloride (6.0 mL) over a period of 15.0 minutes. Stirred for 45.0 minutes, then stirred at room temperature for 120.0 minutes. Quenched reaction with 1N HCl (20.0 mL) and extracted organic with methylene chloride (25.0 mL). Dried organic layer with anhydrous magnesium sulfate, filtered and concentrated filtrate to provide the final title compound, ((2R)-2-phenylpropyl)[(methylethyl)sulfonyl]amine, (1.93 g, 90.1%) an oil; 1H nmr (CDCl3, 300 MHz) δ 1.25 (d, 3H, J=6.9 Hz), 1.29(d, 3H, J=6.9 Hz), 1.30 (d, 3H, J=7.2 Hz), 2.98 (m, 1H), 3.05 (m, 1H), 3.22 (m, 1H), 3.36 (m, 1H), 3.89 (b, 1H), 7.23 (m, 2H), 7.34 (m, 2H).

後処理

  1. temperatureCooled
  2. customreaction to 5° C.
  3. stirringstirred at room temperature for 120.0 minutes
  4. customQuenched
  5. customreaction with 1N HCl (20.0 mL)
  6. extractionextracted organic with methylene chloride (25.0 mL)
  7. filtrationDried organic layer with anhydrous magnesium sulfate, filtered

出典と根拠

ORDレコード
ord-61351087ad0e4e7c8bb28e84a7f0334f
出典データセット
uspto-grants-2004_10
特許番号
US06803484B2

反応ノート

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