1-(Diphenylmethyl)azetidin-3-ol → 1-(Diphenylmethyl)-3-[(2-methylprop-2-en-1-yl)oxy]azetidine

HRID 633905

Reaktionsgleichung

Reaktionsgleichung von HRID 633905
[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]2[CH2:11][CH:10]([OH:12])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:19][C:20]([O-])([CH3:22])[CH3:21].[K+].BrCC(C)=C>C1COCC1.O>[C:13]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:11][CH:10]([O:12][CH2:21][C:20]([CH3:22])=[CH2:19])[CH2:9]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

6

Edukt 3

HCID 3304481-(Diphenylmethyl)azetidin-3-olHCID 3577853-Bromo-2-methyl-1-propeneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 671545541-(Diphenylmethyl)-3-[(2-methylprop-2-en-1-yl)oxy]azetidineAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 1-diphenylmethylazetidin-3-ol (239 mg, 1.0 mmol) in THF (3.6 mL) was cooled to 0° C. t-BuOK (1M in THF, 3.6 mL) was added dropwise and the reaction mixture was stirred at room temperature for 1 h then cooled to 0° C. 3-Bromo-2-methyl-1-propene (504 μL, 5.0 mmol) was added and the solution was stirred from 0° C. to room temperature overnight. The reaction mixture was diluted with H2O and extracted twice with EtOAc. The organic layers were combined, dried over Na2SO4 and concentrated to dryness to give the title compound (276 mg, 94%) as a yellow oil.

Aufarbeitung

  1. additionwas added dropwise
  2. temperaturethen cooled to 0° C
  3. stirringthe solution was stirred from 0° C. to room temperature overnight
  4. extractionextracted twice with EtOAc
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-92e41a9633c344eebac9acbcfa2105f1
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321769B2

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