Diisopropylethylamine → 3-Fluoro-5-trifluoromethylbenzyl 3-oxo-1-isopropylpentane-carboxamide

HRID 1725760Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1725760
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[CH2:5]N.C([N:17](C(C)C)CC)(C)C.[CH:23]([C:26]1([C:32](Cl)=[O:33])[CH2:30][CH2:29][C:28](=[O:31])[CH2:27]1)([CH3:25])[CH3:24]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[CH2:5][C:26]([CH:23]([CH3:25])[CH3:24])([C:32]([NH2:17])=[O:33])[CH2:27][C:28](=[O:31])[CH2:29][CH3:30]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 27333043-Fluoro-5-(trifluoromethyl)benzylamineHCID 186143461-Isopropyl-3-oxocyclopentanoyl chloride

Produkt 1

HCID 867608163-Fluoro-5-trifluoromethylbenzyl 3-oxo-1-isopropylpentane-carboxamideAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 3-fluoro-5-trifluoromethylbenzylamine (3.07 g, 15.9 mmol) and diisopropylethylamine (2.77 mL, 15.9 mmol) in dichloromethane (60 mL) was slowly treated with 1-isopropyl-3-oxocyclopentanoyl chloride (3.0 g, 15.9 mmol) and stirred at ambient temperature overnight. The mixture was diluted with dichloromethane washed with a saturated solution of sodium bicarbonate, 2N HCl, water and brine. The organic phase was dried with anhydrous magnesium sulfate and the solvent was evaporated in vacuo to yield 6.0 g of crude product. This was further purified by column chromatography (silica gel, ethyl acetate hexane (40:60%) to yield 4.10 g (85%) of the pure product. 1H NMR (500 MHz, CDCl3): 7.32 (s, 1H), 7.23 (d, J=8.23 Hz, 1H), 7.19 (d, J=8.93 Hz, 1H), 4.52 (m, 2H), 2.79 (d, J=18.53 Hz, 1H), 2.40 to 2.18 (bm, 4H), 2.0 (m, 2H), 0.98 (d, J=6.63 Hz, 3H), 0.96 (d, 6.60 Hz, 3H).

Aufarbeitung

  1. washwashed with a saturated solution of sodium bicarbonate, 2N HCl, water and brine
  2. dry with materialThe organic phase was dried with anhydrous magnesium sulfate
  3. customthe solvent was evaporated in vacuo
  4. customto yield 6.0 g of crude product
  5. customThis was further purified by column chromatography (silica gel, ethyl acetate hexane (40:60%)

Quellen und Nachweise

ORD-Eintrag
ord-9f09b93ea2a74434a830d23ac7d2666a
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07491737B2

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