Sodium Iodide → 5-(4-Methylsulfonyl-phenyl)-1''-[(1-trifluoromethyl-cyclopropyl)-methyl]-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

HRID 2406341ノート

反応式

HRID 2406341 の反応式
[F:1][C:2]([F:13])([F:12])[C:3]1([CH2:6]OS(C)(=O)=O)[CH2:5][CH2:4]1.[I-].[Na+].[CH3:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[C:28]3[CH2:42][C:33]4([CH2:41][C:35]5([CH2:40][CH2:39][NH:38][CH2:37][CH2:36]5)[CH2:34]4)[O:32][C:29]3=[CH:30][N:31]=2)=[CH:22][CH:21]=1)(=[O:19])=[O:18].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O.O>[CH3:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[C:28]3[CH2:42][C:33]4([CH2:41][C:35]5([CH2:36][CH2:37][N:38]([CH2:6][C:3]6([C:2]([F:1])([F:12])[F:13])[CH2:4][CH2:5]6)[CH2:39][CH2:40]5)[CH2:34]4)[O:32][C:29]3=[CH:30][N:31]=2)=[CH:22][CH:21]=1)(=[O:19])=[O:18]

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 86649942(1-(Trifluoromethyl)cyclopropyl)methyl methanesulfonateHCID 867012015-(4-Methylsulfonyl-phenyl)-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

生成物 1

HCID 721948535-(4-Methylsulfonyl-phenyl)-1''-[(1-trifluoromethyl-cyclopropyl)-methyl]-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A solution of methanesulfonic acid (1-trifluoromethyl-cyclopropyl)methyl ester (45 mg) and sodium iodide (34 mg) in N,N-dimethylformamide (2 mL) is stirred at room temperature for 4 h. 5-(4-Methylsulfonyl-phenyl)-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1′-cyclobutane-3′,4″-piperidine] (HCl salt; 50 mg) and K2CO3 (35 mg) are added and the resulting mixture is heated to 60° C. After stirring the mixture at 60° C. for 4 h, water is added and the mixture is extracted with ethyl acetate. The combined extracts are dried (Na2SO4) and concentrated. The residue is triturated with methanol to give the title compound. LC (method 1): tR=0.82 min; Mass spectrum (ESI+): m/z=507 [M+H]+.

後処理

  1. extractionthe mixture is extracted with ethyl acetate
  2. dry with materialThe combined extracts are dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue is triturated with methanol

出典と根拠

ORDレコード
ord-bc3af0339b074e86b8ffb4d69282f849
出典データセット
uspto-grants-2014_08
特許番号
US08809361B2

反応ノート

読み込み中…