HCID 59596677, Verbindung → methyl (2S)-5-(4-bromophenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate

HRID 2264824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2264824
[NH2:1][C@@H:2]([CH2:7][C:8]#[C:9][C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=1)[C:3]([O:5][CH3:6])=[O:4]>C(#N)C.[Cl-].[Na+].O.[O-]S(C(F)(F)F)(=O)=O.[Ag+]>[Br:16][C:13]1[CH:12]=[CH:11][C:10]([C:9]2[CH2:8][CH2:7][C@@H:2]([C:3]([O:5][CH3:6])=[O:4])[N:1]=2)=[CH:15][CH:14]=1

Komponenten

5

Edukt 1

HCID 59596677HCID 59596677, Verbindung

Produkt 1

HCID 59596717methyl (2S)-5-(4-bromophenyl)-3,4-dihydro-2H-pyrrole-2-carboxylateAusbeute 103 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 76223Silver(I) trifluoromethanesulfonateKatalysatorHCID 6342AcetonitrileLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A solution of methyl (2S)-2-amino-5-(4-bromophenyl)-4-pentynoate (D75, 849 mg, 3.009 mmol) and silver-(I)-triflate in acetonitrile (30 ml) was stirred overnight at room temperature. Then brine was added and the product was extracted with dichloromethane. The combined organic layers were dried (Na2SO4), filtered and evaporated to afford the title compound (874 mg, 96%). UPLC: Rt 0.70 min; MS: (ES/+) m/z: 282, 284 [MH+], C12H12BrNO2 requires 282.

Aufarbeitung

  1. extractionthe product was extracted with dichloromethane
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-470589744cef4057b05d7ec205785450
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855218B2

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