Methanol → Methyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochloride

HRID 432953

Reaktionsgleichung

Reaktionsgleichung von HRID 432953
[OH: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].[CH3:14][O:8][C:7](=[O:9])[C@H:4]1[CH2:3][C@@H:2]([OH:1])[CH2:6][NH:5]1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 440014Cis-4-Hydroxy-D-Proline

Produkt 1

HCID 12764090Methyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochloride

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A suspension of 65.0 g (0.50 mol) of cis4-hydroxy-D-proline in 1500 mL of methanol was cooled to 0° C. and 110 mL (179 g, 1.5 mol) of thionyl chloride was added dropwise at 0-5° C. The mixture was then allowed to warm to room temperature overnight. The volatiles were removed under reduced pressure and the residue was triturated with diethyl ether to afford 98.73 g of crude cis-4-hydroxy-D-proline methyl ester hydrochloride as a white solid.

Aufarbeitung

  1. temperatureto warm to room temperature overnight
  2. customThe volatiles were removed under reduced pressure
  3. customthe residue was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-a21a8726fe624df980a5bf596cf50b51
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06664400B2

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