m-Chloroperbenzoic acid → N-Boc-3-pyrroline oxide

HRID 1952427

Reaktionsgleichung

Reaktionsgleichung von HRID 1952427
[C:1]([N:8]1[CH2:12][CH:11]=[CH:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].ClC1C=CC=C(C(OO)=[O:21])C=1>C(Cl)Cl>[C:1]([N+:8]1([O-:21])[CH2:9][CH:10]=[CH:11][CH2:12]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 5148195tert-Butyl 2,5-dihydro-1H-pyrrole-1-carboxylate

Produkt 1

HCID 86654475N-Boc-3-pyrroline oxideAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of N-Boc-3-pyrroline (1.69 g, 10 mmol) in CH2Cl2 (20 mL) was added m-chloroperbenzoic acid (MCPBA) (˜85%, 5.2 g) in CH2Cl2 (20 mL) dropwise, and stirring was continued at room temperature overnight. The solution was extracted with saturated aqueous NaHCO3, saturated aqueous Na2SO3 and saturated aqueous NaHCO3 successively. The organic layer was dried over Na2SO4 and filtered. The solvent was evaporated and the residue was purified by flash chromatography (20% ethyl acetate in hexane) to give the product as an oil (1.54 g, 82%): 1H NMR (300 MHz, CDCl3) δ 3.77 (dd, J=22, 13 Hz, 2H), 3.66 (m, 2H), 3.31 (dd, J=13, 3 Hz, 2H), 1.44 (s, 9H).

Aufarbeitung

  1. extractionThe solution was extracted with saturated aqueous NaHCO3, saturated aqueous Na2SO3 and saturated aqueous NaHCO3 successively
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customThe solvent was evaporated
  5. customthe residue was purified by flash chromatography (20% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e7aee4d4e5b7416a95b5334203d061ce
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404866B2

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