Methanesulfonyl chloride → 1-tert-Butyl 2-methyl (2S,4R)-4-((methanesulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

HRID 49970

Reaktionsgleichung

Reaktionsgleichung von HRID 49970
[CH3:1][O:2][C:3](=[O:17])[C@@H:4]1[CH2:8][C@@H:7]([OH:9])[CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:17])[C@@H:4]1[CH2:8][C@@H:7]([O:9][S:19]([CH3:18])(=[O:21])=[O:20])[CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11]

Komponenten

4

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 2734883(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Produkt 1

HCID 147726821-tert-Butyl 2-methyl (2S,4R)-4-((methanesulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of trans-N-Boc-4-hydroxy proline methyl ester (17.6 g) (0.072 mol) and TEA (12.5 mL) (0.09 mol) in 100 mL of DCM at 0° C. was slowly added methanesulfonyl chloride (7 mL) (0.09 mol). The temperature was allowed to warm to 20° C., and the mixture was stirred overnight. Insoluble material was removed by filtration and the organic layer washed with water, dried over MgSO4, and evaporated in vacuo to afford the above-titled compound as an oil which solidified upon standing (24 g). NMR(CDCl3, 200 MHz): 5.22 (1H, m), 4.32-4.5 (1H, m), 3.5-3.9 (5H, m), 3.05 (3H, s), 2.5-2.73 (1H, m), 2.15-2.35 (1H, m), 1.35-1.5 (9H).

Aufarbeitung

  1. customat 0° C.
  2. customInsoluble material was removed by filtration
  3. washthe organic layer washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-66ebfcfad78b497c97691701722679dc
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710064B2

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