Diisopropylethylamine → 1-[Bis(4-chlorophenyl)methyl]azetidin-3-ol

HRID 602966

Reaktionsgleichung

Reaktionsgleichung von HRID 602966
Br[CH:2]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][CH:4]=1.[NH:17]1[CH2:20][CH:19]([OH:21])[CH2:18]1.CCN(C(C)C)C(C)C>C(#N)C>[Cl:9][C:6]1[CH:7]=[CH:8][C:3]([CH:2]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[N:17]2[CH2:20][CH:19]([OH:21])[CH2:18]2)=[CH:4][CH:5]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 95197Benzene, 1,1'-(bromomethylene)bis(4chloro-HCID 15142903-Hydroxyazetidine

Produkt 1

HCID 218966141-[Bis(4-chlorophenyl)methyl]azetidin-3-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

The reaction mixture of 22.30 g (70.5 mmol) of 1-[bromo(4-chlorophenyl)methyl]-4-chlorobenzene, 5.67 g (77.6 mmol) of azetidin-3-ol (2) and 18.4 mL (105.75 mmol) of DIEA in 250 mL of acetonitrile was rapidly stirred for 1.5 h at rt to 91° C., Reaction mixture was concentrated to remove solvents and residue was purified by silica gel chromatography with hexanes/ethyl acetate/ammonia (2M in MeOH)=100/30/0.5 to afford the title compound; 1H-NMR(CDCl3) δ 2.03 (br s, 1H), 2.81 (m, 2H), 3.55 (m, 2H), 4.34 (s, 1H), 4.50 (m, 1H), 7.29 (m, 4H), 7.34 (m, 4H).

Aufarbeitung

  1. customReaction mixture
  2. concentrationwas concentrated
  3. customto remove solvents and residue
  4. customwas purified by silica gel chromatography with hexanes/ethyl acetate/ammonia (2M in MeOH)=100/30/0.5

Quellen und Nachweise

ORD-Eintrag
ord-b53cb00b03024e8caaa885dee07e725b
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906652B2

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