Dibutylamine → 3-Chloroalpha-(((2-(3,4-dimethoxyphenyl)-1-methylethyl)amino)methyl) benzenemethanol
反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C@@H:12]([CH2:14]S([O-])(=O)=O)C)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[NH2:19][CH2:20][C@@H:21]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=1)[OH:22].C(NCCCC)CCC.[OH-].[Na+]>>[Cl:29][C:25]1[CH:24]=[C:23]([CH:21]([OH:22])[CH2:20][NH:19][CH:12]([CH3:14])[CH2:11][C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:28]=[CH:27][CH:26]=1参加物
反応条件
- 温度
- 60 °C
実験手順
To 274 mg (1.00 mmol) of (S)-[2-(3,4-dimethoxyphenyl)-1-methylethyl methanesulfonate] were added 206 mg (1.20 mmol) of (R)-2-amino-1-(3-chlorophenyl)ethanol and 194 mg (1.50 mmol) of dibutylamine, and the mixture was stirred at 60° C. for 24 hours under nitrogen atmosphere. The reaction mixture was added with a 10% aqueous solution of sodium hydroxide to be alkaline, and extracted twice with 30 ml of toluene. The toluene extract was dried over anhydrous sodium sulfate, and subjected to distillation of the solvent and to purification with silica gel chromatography to give 190 mg of 1-(3-chlorophenyl)-2-[[2-(3,4-dimethoxyphenyl)-1-methylethyl]amino]ethanol as white crystals (yield: 54%). As a result of isolating and analyzing the isomers by high performance liquid chromatography using an optical resolution column (column: Chiralpack AD (trade name), Daicel Chemical Industries, Ltd.), the optical purity of the objective compound was 95.2% [(R,R)/(R,S)=95.2/4.8].
後処理
- extractionextracted twice with 30 ml of toluene
- extractionThe toluene extract
- dry with materialwas dried over anhydrous sodium sulfate
- distillationsubjected to distillation of the solvent and to purification with silica gel chromatography
出典と根拠
- ORDレコード
- ord-afa154ac347f43f9b1658172a8789b2a
- 出典データセット
- uspto-grants-2001_06
- 特許番号
- US06248573B1
反応ノート
読み込み中…