M-Cresol → (3'S)-1'-[4-(3-methylphenoxy)benzoyl]-1,3'-bipyrrolidine hydrochloride

HRID 1176065ノート

反応式

HRID 1176065 の反応式
F[C:2]1[CH:19]=[CH:18][C:5]([C:6]([N:8]2[CH2:12][CH2:11][C@H:10]([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[CH:20]1[C:25]([OH:26])=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:27].C(=O)([O-])[O-].[K+].[K+].[Cl:34]CCl>CN(C)C=O>[ClH:34].[CH3:27][C:21]1[CH:20]=[C:25]([CH:24]=[CH:23][CH:22]=1)[O:26][C:2]1[CH:19]=[CH:18][C:5]([C:6]([N:8]2[CH2:12][CH2:11][C@H:10]([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:9]2)=[O:7])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 342M-CresolHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 59725829(S)-1,3'-Bipyrrolidin-1'-YL(4-fluorophenyl)methanone

生成物 1

HCID 67141368(3'S)-1'-[4-(3-methylphenoxy)benzoyl]-1,3'-bipyrrolidine hydrochloride

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

A solution of (3′S)-1′-(4-fluorobenzoyl)-1,3′-bipyrrolidine (0.011 g, 0.381 mmol in dimethylformamide was treated with m-cresol (0.127 g, 1.14 mmol) and potassium carbonate (0.105 g, 0.762 mmol), heated to 150° C. via microwave radiation for 20 minutes and cooled to room temperature. The reaction mixture was diluted with dichloromethane, washed sequentially with water and saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The resultant residue was purified by flash column chromatography (silica, methanol:dichloromethane 5:95) to give the free amine of the title product as a yellow oil. This oil was dissolved in isopropanol and diethyl ether (1:10), treated with 1.0N HCl in diethyl ether and filtered. The filter cake was dried to afford the title product as a yellow solid, 0.021 g (16%), identified by NMR and mass spectral analyses. MS [351.3 m/e (M+H)].

後処理

  1. temperaturecooled to room temperature
  2. washwashed sequentially with water and saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified by flash column chromatography (silica, methanol:dichloromethane 5:95)

出典と根拠

ORDレコード
ord-3c01488734b846c89c0b823403ce476f
出典データセット
uspto-grants-2010_11
特許番号
US07842715B2

反応ノート

読み込み中…