Ammonium Chloride → HCID 70234416, Verbindung

HRID 850607

Reaktionsgleichung

[CH2:1]([NH:8][C@H:9]([CH3:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:22]([O:26][C:27](=[O:37])[CH:28]=[CH:29][C:30]1[CH:31]=[N:32][C:33]([NH2:36])=[CH:34][CH:35]=1)([CH3:25])([CH3:24])[CH3:23].[NH4+].[Cl-]>C1COCC1>[C:22]([O:26][C:27](=[O:37])[CH2:28][C@@H:29]([C:30]1[CH:31]=[N:32][C:33]([NH2:36])=[CH:34][CH:35]=1)[N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@@H:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:16])([CH3:25])([CH3:23])[CH3:24]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a cooled (0° C.) solution of (R)-(+)-N-benzyl-α-methylbenzylamine (4.0 g, 19 mmol) in 50 mL THF was gradually added n-butyllithium (11.3 mL, 2.5 M, 28.2 mmol) over 5 min. The mixture was stirred for 30 min at 0° C. and cooled to -78° C. A solution of 9-2 (2.0 g, 9.4 mmol) in 20 mL THF was gradually added. After stirring for 40 min at -78° C., it was treated with NH4Cl (sat.) at -78° C., warmed to room temperature and extracted three times with EtOAc. The combined organic layers were washed with brine and dried over Na2SO4. After solvent evaporation, the residue was purified using silica gel flash chromatography (EtOAc/hexanes, 1:2) to afford the desired product 9-3 as an oil.

Aufarbeitung

customover 5 min
temperaturecooled to -78° C
stirringAfter stirring for 40 min at -78° C.
temperaturewarmed to room temperature
extractionextracted three times with EtOAc
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
customAfter solvent evaporation
customthe residue was purified

Quellen und Nachweise

ORD-Eintrag: ord-a3a1a044c4b7454fab5ee1e58e0d02ce
Quelldatensatz: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06017926

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