1-Chloroethyl chloroformate → 3-[2-(Trifluoromethyl)-4'-(difluoromethoxy)benzhydryloxy]azetidine hydrochloride

HRID 1785721Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1785721
C([N:14]1[CH2:17][CH:16]([O:18][CH:19]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH:37]([F:39])[F:38])=[CH:32][CH:31]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]([F:29])([F:28])[F:27])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cl:40]C(OC(Cl)C)=O>C(Cl)Cl>[ClH:40].[F:29][C:26]([F:27])([F:28])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH:19]([O:18][CH:16]1[CH2:17][NH:14][CH2:15]1)[C:30]1[CH:35]=[CH:34][C:33]([O:36][CH:37]([F:38])[F:39])=[CH:32][CH:31]=1

Komponenten

4

Edukt 2

HCID 5213051-Chloroethyl chloroformateHCID 689036941-Benzhydryl-3-[2-(trifluoromethyl)-4'-(difluoromethoxy)-benzhydryloxy]azetidine

Produkt 1

HCID 866111663-[2-(Trifluoromethyl)-4'-(difluoromethoxy)benzhydryloxy]azetidine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-benzhydryl-3-[2-(trifluoromethyl)-4′-(difluoro-methoxy)benzhydryloxy]azetidine (174) (2.73 g from previous step-assumed 4.7 mmol) in DCM (40 mL), cooled in ice-water bath, was added 1-chloroethyl chloroformate (1 mL, 9.4 mmol). After 1 h, the mixture was allowed to warm to ambient temperature. After a further 5.5 h, the mixture was concentrated under reduced pressure, methanol (40 mL) was added, and the mixture was stirred for 16 h. The mixture was concentrated under reduced pressure, then dissolved in iso-hexane (4 mL)-DIPE (30 mL)-MeOH (2 mL). Upon stirring, a precipitate formed. The mixture was cooled in ice-water bath for 15 min.

Aufarbeitung

  1. waitAfter a further 5.5 h
  2. concentrationthe mixture was concentrated under reduced pressure, methanol (40 mL)
  3. additionwas added
  4. concentrationThe mixture was concentrated under reduced pressure
  5. dissolutiondissolved in iso-hexane (4 mL)-DIPE (30 mL)-MeOH (2 mL)
  6. stirringUpon stirring
  7. customa precipitate formed

Quellen und Nachweise

ORD-Eintrag
ord-50c20bd30b5747c1b945b789e9d83ef9
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07504522B2

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