Ethanol → 3-[1-(2,3-Dichlorophenoxy)-3-methylsulfanylpropyl]pyrrolidine

HRID 1254998

반응식

HRID 1254998 반응식
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([CH:13]([OH:18])[CH2:14][CH2:15][S:16][CH3:17])[CH2:9]1)=O)(C)(C)C.[H-].[Na+].[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24](F)[C:23]=1[Cl:29].CCO>CN(C=O)C.Cl>[Cl:21][C:22]1[C:23]([Cl:29])=[CH:24][CH:25]=[CH:26][C:27]=1[O:18][CH:13]([CH:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)[CH2:14][CH2:15][S:16][CH3:17]

참가 물질

7

반응물 4

HCID 702EthanolHCID 24758Sodium hydride2회HCID 119011Benzene, 1,2-dichloro-3-fluoro-HCID 668597603-(1-Hydroxy-3-methylsulfanylpropyl)pyrrolidine-1-carboxylic Acid t-Butyl Ester

생성물 1

HCID 581202633-[1-(2,3-Dichlorophenoxy)-3-methylsulfanylpropyl]pyrrolidine

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 6228Dimethylformamide용매

실험 절차

3-(1-Hydroxy-3-methylsulfanylpropyl)pyrrolidine-1-carboxylic acid t-butyl ester (49 mg, 180 mmol) was dissolved in DMF (550 μL). 60% NaH in oil (60:40, NaH:mineral oil, 8.5 mg, 210 μmol) was slowly added, and the mixture was stirred for 15 minutes at room temperature. 1,2-Dichloro-3-fluorobenzene (62 μL, 530 μmol) was added, and the resulting mixture was heated at 90° C. for 24 hours. The reaction was quenched with MeOH, and DMF/MeOH was removed in vacuo. The product was dissolved in 1.25M HCl in EtOH (1.4 mL, 1.8 mmol) and stirred overnight at room temperature. The product was then purified by preparative HPLC to yield the title compound as a mixture of all 4 stereoisomers (R,R, R,S, S,S, and S,R) as mono-TFA salts (20 mg, 100% purity). MS m/z: [M+H]+ calcd for C14H19Cl2NOS, 320.06. found 320.0.

후처리

  1. temperaturethe resulting mixture was heated at 90° C. for 24 hours
  2. customThe reaction was quenched with MeOH, and DMF/MeOH
  3. customwas removed in vacuo
  4. stirringstirred overnight at room temperature
  5. customThe product was then purified by preparative HPLC

출처 및 근거

ORD 기록
ord-f292b0e4231d40778223fddf3fe3aa8c
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455665B2

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