Water → 4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]phenylethylsulfone

HRID 1622184ノート

反応式

HRID 1622184 の反応式
Cl.Cl.[C:3]1([C@H:13]([NH:15][C@H:16]2[CH2:20][CH2:19][NH:18][CH2:17]2)[CH3:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.F[C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][S:30]([CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38](F)=[CH:37][CH:36]=2)(=[O:32])=[O:31])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O.C(Cl)(Cl)Cl>[C:3]1([C@H:13]([NH:15][C@H:16]2[CH2:20][CH2:19][N:18]([C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][S:30]([CH2:33][CH2:34][C:35]4[CH:40]=[CH:39][C:38]([N:18]5[CH2:19][CH2:20][C@H:16]([NH:15][C@@H:13]([C:3]6[C:12]7[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=7)[CH:6]=[CH:5][CH:4]=6)[CH3:14])[CH2:17]5)=[CH:37][CH:36]=4)(=[O:32])=[O:31])=[CH:24][CH:23]=3)[CH2:17]2)[CH3:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 534437264-FluorophenylethylsulfoneHCID 67408696(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidine dihydrochloride

生成物 1

HCID 674070244-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]phenylethylsulfone収率 73.7%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 6212Chloroform溶媒

反応条件

温度
130 °C

実験手順

To a solution of 150 mg of (S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidine dihydrochloride and 108 mg of 4-fluorophenylethylsulfone in 2 ml of DMSO was added 263 mg of potassium carbonate, and the reaction mixture was stirred at 130° C. for 1 day. To the reaction mixture was added water and chloroform, the mixture was stirred and the liquids were separated. The organic layer was dried and evaporated, and then, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=80:20→40:60) to obtain 132.5 mg of 4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]phenylethylsulfone.

後処理

  1. stirringthe mixture was stirred
  2. customthe liquids were separated
  3. customThe organic layer was dried
  4. customevaporated
  5. customthe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=80:20→40:60)

出典と根拠

ORDレコード
ord-585e3ab3623f4b149a0a72ce19855af3
出典データセット
uspto-grants-2014_07
特許番号
US08778628B2

反応ノート

読み込み中…