Trifluoroacetic acid → 1-(3-(4-Nitrophenyl)azetidin-1-yl)propan-1-one

HRID 1260235Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1260235
C(O[C:6]([N:8]1[CH2:11][CH:10]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[CH2:9]1)=[O:7])(C)(C)C.[C:21](O)([C:23](F)(F)F)=O.C(Cl)(=O)CC.C(N(CC)CC)C>C(Cl)Cl.C1COCC1>[N+:18]([C:15]1[CH:14]=[CH:13][C:12]([CH:10]2[CH2:9][N:8]([C:6](=[O:7])[CH2:21][CH3:23])[CH2:11]2)=[CH:17][CH:16]=1)([O-:20])=[O:19]

Komponenten

7

Edukt 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 57470079HCID 57470079, Verbindung

Produkt 1

HCID 574700801-(3-(4-Nitrophenyl)azetidin-1-yl)propan-1-oneAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Using the same procedure as described in 46.4, 3-(4-nitro-phenyl)-azetidine-1-carboxylic acid tert-butyl ester was deprotected with TFA (15 ml) in CH2Cl2 (100 ml) and the resulting amine treated with propionyl chloride (2900, 3.31 mmol) and triethylamine (470 μl, 3.37 mmol) in THF (80 ml). Purification of the crude product by flash column chromatography (heptane:ethyl acetate, 1:1) provides the title compound (570 mg, 87% for two steps) as a brown oil.

Aufarbeitung

  1. customPurification of the crude product by flash column chromatography (heptane:ethyl acetate, 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-a337fec6db594671a88a89e26a7c4f14
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470810B2

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