Methanesulfonyl chloride → (2S,4R)-1-Benzyl 2-methyl 4-((methylsulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

HRID 54620

Reaktionsgleichung

Reaktionsgleichung von HRID 54620
[CH3:1][O:2][C:3](=[O:20])[C@@H:4]1[CH2:8][C@@H:7]([OH:9])[CH2:6][N:5]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>N1C=CC=CC=1.ClCCl>[CH3:1][O:2][C:3](=[O:20])[C@@H:4]1[CH2:8][C@@H:7]([O:9][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:6][N:5]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]

Komponenten

5

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 6884112-Methyl 1-(phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

Produkt 1

HCID 11725861(2S,4R)-1-Benzyl 2-methyl 4-((methylsulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The product from Example 11 (50.0 g; 178 mmol) is dissolved in anhydrous pyridine (910 ml). Methanesulphonyl chloride (18.6 ml; 241 mmol) is added dropwise while cooling in ice. Subsequently, the solution is stirred for 2.5 h during which it is allowed to warm to room temperature. The solution is then diluted with dichloromethane (3.6 l) and extracted twice by shaking with a 10% solution of sodium hydrogen carbonate (1.1 l on each occasion). The organic phase is dried (magnesium sulphate), concentrated and the residue subsequently distilled repeatedly with toluene. Yield: 64.0 g (quantitative).

Aufarbeitung

  1. temperaturewhile cooling in ice
  2. extractionextracted twice
  3. stirringby shaking with a 10% solution of sodium hydrogen carbonate (1.1 l on each occasion)
  4. dry with materialThe organic phase is dried (magnesium sulphate)
  5. concentrationconcentrated
  6. distillationthe residue subsequently distilled repeatedly with toluene

Quellen und Nachweise

ORD-Eintrag
ord-f4ab2fa399ac4a6ea69048ab269bac74
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05623049

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