Diisopropylethylamine → rac-(2R,3aR,6aR)-2-(4-{[(2-Fluorophenyl)methyl]oxy}phenyl)-1,5-bis(phenylmethyl)hexahydropyrrolo[3,4-b]pyrrol-6(1H)-one

HRID 2264838Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2264838
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1.[C:18]1([CH2:24][N:25]([CH2:37][CH:38]=[CH2:39])[C:26](=[O:36])[CH2:27][NH:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]2[N:28]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:27]3[C:26](=[O:36])[N:25]([CH2:24][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:37][CH:38]3[CH2:39]2)=[CH:12][CH:11]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 7027174-((2-Fluorophenyl)methoxy)benzaldehydeHCID 59596664N-Allyl-N-benzyl-2-(benzylamino)acetamide

Produkt 1

HCID 68409482rac-(2R,3aR,6aR)-2-(4-{[(2-Fluorophenyl)methyl]oxy}phenyl)-1,5-bis(phenylmethyl)hexahydropyrrolo[3,4-b]pyrrol-6(1H)-oneAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A solution of 4-{[(2-fluorophenyl)methyl]oxy}benzaldehyde (D92, 920 mg, 4.0 mmol), prepared by an analogous procedure to that described hereinabove, N1,N2-bis(phenylmethyl)-N1-2-propen-1-ylglycinamide (D90, 588 mg, 2.0 mmol) and DIPEA (0.68 ml, 4.0 mmol) in dry toluene (8 ml) were stirred at 120° C. for 72 h. After the reaction was terminated, it was cooled to room temperature, diluted with ethyl acetate and washed with water and brine. The residue was purified via flash chromatography affording the title compound (503 mg, 50%) as a racemate. Rf (cyclohexanes:ethyl acetate 1:1): 0.57.

Aufarbeitung

  1. customAfter the reaction was terminated
  2. temperatureit was cooled to room temperature
  3. additiondiluted with ethyl acetate
  4. washwashed with water and brine
  5. customThe residue was purified via flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d9be2795f9b34b578340ef68136db130
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855218B2

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