Methanol → HCID 53420628, Verbindung

HRID 1013742Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1013742
[F:1][C@H:2]1[CH2:6][NH:5][C@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.S(Cl)([Cl:12])=O.[CH3:14]O>>[ClH:12].[F:1][CH:2]1[CH2:6][NH:5][CH:4]([C:7]([O:9][CH3:14])=[O:8])[CH2:3]1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 11902999(4R)-4-Fluoro-L-proline

Produkt 1

HCID 53420628HCID 53420628, Verbindung

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A round bottom flask was charged with (2S,4R)-4-fluoropyrrolidine-2-carboxylic acid (300 mg, 2254 μmol) and 22 mL MeOH. The heterogeneous mixture was cooled to 0° C. under nitrogen, and thionyl chloride (181 μl, 2479 μmol) was added dropwise. The reaction mixture was allowed to warm slowly to RT, and stirring was continued overnight at 65° C. The mixture was concentrated under high vacuum to provide methyl 4-fluoropyrrolidine-2-carboxylate hydrochloride as a mixture of the (2S,4R) and (2R,4R) diastereomers, confirmed by 1H and 13C NMR.

Aufarbeitung

  1. temperatureto warm slowly to RT
  2. concentrationThe mixture was concentrated under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-010488eba6cf4a2d825ef6ebca761bbf
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981891B2

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