1-Chloroethyl chloroformate → 3-(4-Fluorophenoxy)azetidine

HRID 72423

Reaktionsgleichung

Reaktionsgleichung von HRID 72423
ClC(OC(Cl)C)=O.C([N:21]1[CH2:24][CH:23]([O:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[CH2:22]1)(C1C=CC=CC=1)C1C=CC=CC=1>ClCCCl>[F:32][C:29]1[CH:30]=[CH:31][C:26]([O:25][CH:23]2[CH2:22][NH:21][CH2:24]2)=[CH:27][CH:28]=1

Komponenten

4

Edukt 2

HCID 5213051-Chloroethyl chloroformateHCID 150533691-Benzhydryl-3-(4-fluorophenoxy)azetidine

Produkt 1

HCID 214287303-(4-Fluorophenoxy)azetidineAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

1-chloroethyl chloroformate (0.87 ml, 8.09 mmol) was added to an ice-cooled solution of 1-benzhydryl-3-(4-fluorophenoxy)azetidine (D21) (1.8 g, 5.39 mmol) in 1,2 dichloroethane (18 ml) and the resulting mixture was heated under reflux for 3 hours. The reaction mixture was evaporated in vacuo and the residue was re-dissolved in methanol (10 ml). This solution was heated under reflux overnight then cooled at room temperature and evaporated in vacuo. The obtained residue was loaded on SPE-SCX (20 g) cartridge. The ammonia fractions, after evaporation in vacuo, were loaded on by SPE-Si (5 g) cartridge eluting with a mixture dichloromethane/dichloromethane:NH3 (2M solution in MeOH) (from 100/0 to 80/20). Collected fractions after solvent evaporation afforded the title compound (D49) (0.9 g)

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customThe reaction mixture was evaporated in vacuo
  4. dissolutionthe residue was re-dissolved in methanol (10 ml)
  5. temperatureThis solution was heated
  6. temperatureunder reflux overnight
  7. customevaporated in vacuo
  8. customThe ammonia fractions, after evaporation in vacuo
  9. washeluting with a mixture dichloromethane/dichloromethane
  10. customCollected fractions after solvent evaporation

Quellen und Nachweise

ORD-Eintrag
ord-c055887e6a81427db20809de6ebda7cf
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828987B2

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