2-(Dibenzylamino)-3-phenylpropanal → HCID 69017313, Verbindung

HRID 1436491

Reaktionsgleichung

Reaktionsgleichung von HRID 1436491
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH3:17])[C:13](=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:29]([N:36]([CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[CH:37]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH:38]=[O:39])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1COCC1>[CH2:47]([N:36]([CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C@@H:37]([CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[CH:38]([CH:12]1[N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:16][CH2:15][N:14]([CH3:17])[C:13]1=[O:18])[OH:39])[C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1

Komponenten

5

Edukt 3

HCID 5638962-(Dibenzylamino)-3-phenylpropanalHCID 2733832Lithium HexamethyldisilazideHCID 586385404-Cbz-1-methyl-2-piperazinone

Produkt 1

HCID 69017313HCID 69017313, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Treat a solution of 4-benzyloxycarbonyl-1-methylpiperazin-2-one (1.4 g, 5.7 mmol) in THF (4 mL) cooled at −78° C. with lithium bis(trimethylsilyl)amide (1.0 M solution in THF, 5.7 mL, 5.7 mmol) dropwise and stir 30 min. Add 2-(dibenzylamino)-3-phenylpropanal (1 g, 3.1 mmol) in THF (2 mL) and stir at −78° C. for 45 min. Quench with saturated aqueous ammonium chloride solution. Separate organic layer and wash with water, saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 1:1 hexanes:ethyl acetate) to provide the title compound as a mixture of four diastereoisomers which are separated by HPLC (normal phase, eluting with 85:15 hexanes:isopropanol) (828 mg, 45% total yield).

Aufarbeitung

  1. customQuench with saturated aqueous ammonium chloride solution
  2. washSeparate organic layer and wash with water, saturated aqueous sodium chloride
  3. dry with materialdry (magnesium sulfate)
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 1:1 hexanes:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d8ad7685d0a5440d903e8acc8f90740a
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618978B2

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