Dimethyl Sulfoxide → tert-Butyl (2S)-2-isopropyl-4-oxopyrrolidine-1-carboxylate

HRID 81130Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 81130
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][C@H:12]1[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:14]([CH:24]([CH3:26])[CH3:25])[CH2:13]1.C(N(CC)CC)C>C(Cl)Cl>[O:11]=[C:12]1[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[C@H:14]([CH:24]([CH3:26])[CH3:25])[CH2:13]1

Komponenten

6

Edukt 4

HCID 679Dimethyl Sulfoxide2×HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 60054987tert-butyl (2S,4R)-4-hydroxy-2-(propan-2-yl)pyrrolidine-1-carboxylate2×

Produkt 1

HCID 26967714tert-Butyl (2S)-2-isopropyl-4-oxopyrrolidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Oxalyl chloride (16 mL) dissolved in DCM (200 mL) was placed in a three-neck flask equipped with a stirrer and two addition funnels. One funnel contained DMSO (23 mL) in DCM (100 mL) and the other tert-butyl (2S,4R)-4-hydroxy-2-(propan-2-yl)pyrrolidine-1-carboxylate (37 g) in DCM (100 mL). The contents of the flask were cooled to −78° C., and the DMSO solution was added dropwise. After 15 minutes, tert-butyl (2S,4R)-4-hydroxy-2-(propan-2-yl)pyrrolidine-1-carboxylate was added. The reaction mixture was stirred for 30 minutes, and triethylamine (110 mL) was added. The cooling bath was removed, and water (100 mL) was added at room temperature and stirred for 10 minutes. The organic layer was separated, and the aqueous layer was extracted with DCM (3×100 mL). The combined organic layers were washed with brine (3×50 mL), dried over magnesium sulfate, filtered, and concentrated. The material was purified by silica gel chromatography (petroleum ether/ethyl acetate, 15/1) to afford tert-butyl (2S)-4-oxo-2-(propan-2-yl)pyrrolidine-1-carboxylate.

Aufarbeitung

  1. customwas placed in a three-neck flask
  2. customequipped with a stirrer
  3. additiontwo addition funnels
  4. customThe cooling bath was removed
  5. additionwater (100 mL) was added at room temperature
  6. stirringstirred for 10 minutes
  7. customThe organic layer was separated
  8. extractionthe aqueous layer was extracted with DCM (3×100 mL)
  9. washThe combined organic layers were washed with brine (3×50 mL)
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe material was purified by silica gel chromatography (petroleum ether/ethyl acetate, 15/1)

Quellen und Nachweise

ORD-Eintrag
ord-ce7afa214b8e456095e7ffbcf783120d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846657B2

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