Methanesulfonyl chloride → tert-Butyl 3-(((methylsulfonyl)oxy)methyl)pyrrolidine-1-carboxylate

HRID 640000

Reaktionsgleichung

Reaktionsgleichung von HRID 640000
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH:8]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:1][S:2]([O:6][CH2:7][CH:8]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]1)(=[O:4])=[O:3]

Komponenten

5

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 5237175tert-Butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

Produkt 1

HCID 4183641tert-Butyl 3-(((methylsulfonyl)oxy)methyl)pyrrolidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methane sulphonyl chloride (0.39 ml, 5.0 mmol) was added dropwise to a solution of tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate (0.51 g, 2.5 mmol) and 4-(dimethylamino)pyridine (0.61 g, 5.0 mmol) in dichloromethane (15 ml). The mixture was stirred at room temperature for 30 minutes and then concentrated to approximately half volume and purified by silica gel chromatography. Elution with a mixture of 3:1 to 1:1 iso-hexane:ethyl acetate yielded tert-butyl 3-{[(methylsulphonyl)oxy]methyl}pyrrolidine-1-carboxylate.

Aufarbeitung

  1. concentrationconcentrated to approximately half volume
  2. custompurified by silica gel chromatography
  3. washElution
  4. additionwith a mixture of 3:1 to 1:1 iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-262b180d5bd640469039c50ef630a6ce
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691867B2

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