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 2406341노트

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HRID 2406341 반응식
[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]

참가 물질

7

반응물 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]

생성물 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]

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-bc3af0339b074e86b8ffb4d69282f849
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08809361B2

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