1,2-Dichloroethane → Tert-butyl 4-(3-oxopyrrolidin-1-yl)benzoate

HRID 1907741Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1907741
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:19]=[CH:18][C:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:9][CH:8]=2)[CH2:3]1.C[N+]1([O-])CCOCC1.ClCCCl>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[O:1]=[C:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:19]=[CH:18][C:10]([C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])=[CH:9][CH:8]=2)[CH2:3]1

Komponenten

6

Edukt 3

HCID 111,2-DichloroethaneHCID 82029Methyl morpholine oxideHCID 10084125Tert-butyl 4-(3-hydroxypyrrolidin-1-yl)benzoate

Produkt 1

HCID 10015517Tert-butyl 4-(3-oxopyrrolidin-1-yl)benzoateAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178419074HCID 178419074, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of alcohol 266 (2.75 g, 10.45 mmol), NMO (5.8 g, 49 mmol) and 4 Å molecular sieves (8.34 g) was suspended in dry DCM (100 mL) and dry 1,2-dichloroethane (100 mL), stirred at room temperature for 45 min, and then cooled to 0° C. for the addition of solid TPAP (0.36 g, 1.03 mmol). The reaction mixture was stirred at 0° C. for 30 min and then at room temperature for 5 h, filtered through Celite®/silica gel using 50% AcOEt in hexanes as an eluent, then concentrated. The residue was purified by flash chromatography (eluent: 30% to 50% AcOEt in hexane) to provide title compound 267 (0.78 g, 29% yield).

Aufarbeitung

  1. waitat room temperature for 5 h
  2. filtrationfiltered through Celite®/silica gel using 50% AcOEt in hexanes as an eluent
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography (eluent: 30% to 50% AcOEt in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-7669fc4976394115afbe12a321938740
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598168B2

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