Hydrochloric Acid → (S)-3-[(S)-1-(2,3-Dichlorophenoxy)butyl]pyrrolidine

HRID 587997

反応式

HRID 587997 の反応式
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([C@@H:13]([OH:17])[CH2:14][CH2:15][CH3:16])[CH2:9]1)=O)(C)(C)C.CN(C=O)C.[H-].[Na+].[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28](F)[C:27]=1[Cl:33].Cl.CCO>>[Cl:25][C:26]1[C:27]([Cl:33])=[CH:28][CH:29]=[CH:30][C:31]=1[O:17][C@H:13]([C@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)[CH2:14][CH2:15][CH3:16]

参加物

7

反応物 6

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 119011Benzene, 1,2-dichloro-3-fluoro-HCID 58104616(S)-3-((S)-1-Hydroxybutyl)pyrrolidine-1-carboxylic Acid t-Butyl Ester

生成物 1

HCID 58104605(S)-3-[(S)-1-(2,3-Dichlorophenoxy)butyl]pyrrolidine

実験手順

(S)-3-((S)-1-Hydroxybutyl)pyrrolidine-1-carboxylic acid t-butyl ester (50 mg, 0.2 mmol) was dissolved in DMF (1.0 mL, 13 mmol). NaH (5.9 mg, 246 μmol) was slowly added and the mixture was stirred at room temperature for 15 minutes. 1,2-Dichloro-3-fluorobenzene (67.8 mg, 411 μmol) was added. The mixture was stirred at 70° C. for 3 hours, then concentrated. 1.2M HCl in EtOH (1.0 mL, 1.2 mmol) was added, and the mixture was stirred overnight. The product was concentrated and purified by preparative HPLC to yield the title compound as a mono-TFA salt (19 mg, 100% purity). MS in/z: [M+H]+ calcd for C14H19Cl2NO, 288.08. found 288.0.

後処理

  1. stirringThe mixture was stirred at 70° C. for 3 hours
  2. concentrationconcentrated
  3. stirringthe mixture was stirred overnight
  4. concentrationThe product was concentrated
  5. custompurified by preparative HPLC

出典と根拠

ORDレコード
ord-96b8c89da0184a5c8dbd7b004e8fd8bf
出典データセット
uspto-grants-2016_01
特許番号
US09227933B2

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