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

HRID 2085452ノート

反応式

HRID 2085452 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][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

7

反応物 4

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

生成物 1

HCID 11481889((2R)-2-phenylpropyl)[(methylethyl)sulfonyl]amine収率 92%

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 (1.2g, 8.87mmol) in hexane (16.0 mL) was added triethylamine (2.47 mL, 17.74 mmol) and 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 IN 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=6.9Hz), 1.29(d, 3H, J=6.9Hz), 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 IN 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-1295869916a84999809be9b534370de8
出典データセット
uspto-grants-2004_04
特許番号
US06720357B2

反応ノート

読み込み中…