Tert-butyl cinnamate → (3R,alphaS)-t-Butyl 3-(N-cinnamyl-alpha-methylbenzylamino)-3-phenylpropionate

HRID 1637036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1637036
[CH2:1]([NH:10][C@@H:11]([CH3:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([Li])CCC.[C:24]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])(=[O:33])[CH:25]=[CH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH2:1]([N:10]([C@@H:11]([CH3:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C@@H:26]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH2:25][C:24]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

4

Edukt 3

HCID 347555Tert-butyl cinnamateHCID 54105238(S)-N-cinnamyl-alpha-methylbenzylamineHCID 178418339Butyllithium

Produkt 1

HCID 86755225(3R,alphaS)-t-Butyl 3-(N-cinnamyl-alpha-methylbenzylamino)-3-phenylpropionateAusbeute 93,8 %

Versuchsvorschrift

(S)-N-cinnamyl-α-methylbenzylamine (4) (0.100 g, 0.42 mmol), 1.6M butyllithium (0.242 ml, 0.39 mmol) and t-butyl cinnamate (7) (0.072 g, 0.35 mmol) were reacted according to the procedure of Example 1. Flash chromatography of the product on silica gel [ethyl acetate/petroleum ether (1:49)] afforded the title compound (Rf 0.3) as a colourless oil (0.145 g, 78%). δH (300 MHz; CDCl3) 7.50-7.18 (15H, m, Ph), 6.42 (1H, d, J=16.0, PhCH=CH), 6.11 (1H, dt, J=16.0 and 6.2; CH=CHPh), 4.53 (1H, dd, J=8.7 and 6.4, PhCHCH2), 4.07 (1H, q, J=6.7, PhCHCH3), 3.32 (2H, dd, J=6.2 and 1.1, NCH2), 2.83 (1H, dd, J=14.6 and 6.4, CH2CO2), 2.62 (1H, dd, J=14.6 and 8.7, CH2CO2), 1.31 (9H, s, (CH3)3C), 1.27 (3H, d, J=6.7, PhCHCH3).

Quellen und Nachweise

ORD-Eintrag
ord-294dd245f02f4549a0825dda711e88ed
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06037498

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