Tetrahydrofuran → 1-(Diphenylmethyl)azetidin-3-yl methanesulfonate

HRID 82960

Reaktionsgleichung

Reaktionsgleichung von HRID 82960
[CH2:1]([CH:8]1[CH:11](O)[CH:10]([CH2:13][C:14]2[CH:19]=CC=CC=2)N1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22].C([N:27]([CH2:30][CH3:31])[CH2:28]C)C.C1C[O:35]CC1>>[CH3:20][S:21]([O:23][CH:31]1[CH2:28][N:27]([CH:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:8]2[CH:11]=[CH:10][CH:13]=[CH:14][CH:19]=2)[CH2:30]1)(=[O:35])=[O:22]

Komponenten

5

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 131731899Dibenzylazetidin-3-ol

Produkt 1

HCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonateAusbeute 92 %

Versuchsvorschrift

To a solution of dibenzylazetidin-3-ol (500 mg, 2.09 mmol) in THF (21 mL) at 0° C. under nitrogen was added methanesulfonyl chloride (194 μL, 2.51 mmol) and triethylamine (612 μL, 4.39 mmol). The reaction mixture was stirred for 1 h then concentrated to dryness. The residue was dissolved in dichloromethane, washed with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated to dryness to give the title product (0.61 g, 92%) as a yellow oil.

Aufarbeitung

  1. concentrationthen concentrated to dryness
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-61c31edeb8ca44868d045b53dca99afb
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846711B2

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