Bicyclo(2.2.1)heptan-2-one → 1-Methyl-5-[3-(Bicyclo[2.2.1]hept-2-ylamino)-4-Methoxyphenyl]-2-Imidazolidinone

HRID 653651

Reaktionsgleichung

[CH3:1][N:2]1[CH:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([NH2:15])[CH:8]=2)[CH2:5][NH:4][C:3]1=[O:16].[CH2:17]1[CH:21]2[CH2:22][C:23](=O)[CH:19]([CH2:20]2)[CH2:18]1.C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C.CCOCC.C(OCC)(=O)C>[CH3:1][N:2]1[CH:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([NH:15][CH:18]3[CH2:17][CH:21]4[CH2:20][CH:19]3[CH2:23][CH2:22]4)[CH:8]=2)[CH2:5][NH:4][C:3]1=[O:16]

Komponenten

Reaktionsbedingungen

Temperatur: 5 °C

Versuchsvorschrift

The aniline of Example 51 (3.07 g, 17.95 mmol) is dissolved in 60 ml of glacial acetic acid and to this is added norcamphor (2.37 g, 21.54 mmol). The reaction is cooled to 5° C. and to it is added sodium cyanoborohydride (1.36 g, 21.54 mmol). The reaction is poured onto ice and is pH adjusted to 7 with 1 normal NaOH solution. The aqueous is extracted with methylene chloride dried over MgSO4, filtered and concentrated in vacuo to afford a brown oil which is flashed on SiO2 with ethyl acetate as the eluent. The appropriate fractions are combined and concentrated in vacuo to yield a white paste which is tritarted with ether to yield 0.57 g (10%) of the product as a white crystalline solid. MP=171°-174° C.

Aufarbeitung

additionThe reaction is poured onto ice
extractionThe aqueous is extracted with methylene chloride
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customto afford a brown oil which
concentrationconcentrated in vacuo
customto yield a white paste which

Quellen und Nachweise

ORD-Eintrag: ord-13bf42b1e6354808aa135d37f62e2de0
Quelldatensatz: uspto-grants-1992_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05128358

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