4-Methylmorpholine → 1-(Diphenylmethyl)azetidin-3-one

HRID 605701

Reaktionsgleichung

Reaktionsgleichung von HRID 605701
Cl.[C:2]1([CH:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:9]2[CH2:12][CH:11]([OH:13])[CH2:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.C[N+]1([O-])CCOCC1.C(OCC)(=O)C>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[C:14]1([CH:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[N:9]2[CH2:12][C:11](=[O:13])[CH2:10]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 8857Ethyl AcetateHCID 82029Methyl morpholine oxideHCID 28017261-benzhydrylazetidin-3-ol Hydrochloride

Produkt 1

HCID 37355581-(Diphenylmethyl)azetidin-3-oneAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178419074HCID 178419074, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-(Diphenylmethyl)azetidin-3-ol hydrochloride (2.75 g, 9.98 mmol), prepared using procedures similar to those described for Scheme 1 of the General Synthetic Section, 3 Å molecular sieves and 4-methylmorpholine (1.1 mL, 10.0 mmol) were suspended in dichloromethane (20 mL) at 0° C. 4-Methylmorpholine N-oxide (2.93 g, 25.0 mmol) and tetrapropylammonium perruthenate (140 mg, 0.399 mmol) were added and the mixture was stirred at ambient for 24 h. The mixture was filtered through a plug of silica using 5% triethylamine in ethyl acetate as eluent. The filtrate was concentrated in vacuo and the residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic portion was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Column chromatography (silica gel, 8:1 hexanes:ethyl acetate) gave 1-(diphenylmethyl)azetidin-3-one (871 mg, 3.68 mmol, 37% yield): 1H NMR (400 MHz, CDCl3): 7.50-7.46 (m, 4H), 7.33-7.27 (m, 4H), 7.27-7.19 (m, 2H), 4.59 (s, 1H), 4.01 (s, 4H); MS (EI) for C16H15NO: 238 (MH+).

Aufarbeitung

  1. filtrationThe mixture was filtered through a plug of silica using 5% triethylamine in ethyl acetate as eluent
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  4. washThe organic portion was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-38235d1b3823428da89e2cee2812fd2e
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915250B2

Verknüpfte Notizen

Wird geladen…