HCID 66833546, Verbindung → 3-{2-[(Tert-butoxy)carbonyl]-1,2,3,4-tetrahydroisoquinolin-3-yl}propanoic acid
Reaktionsgleichung
C([O:3][C:4](=[O:24])/[CH:5]=[CH:6]/[CH:7]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][N:8]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])C>C(O)C.[Pd]>[C:20]([O:19][C:17]([N:8]1[CH:7]([CH2:6][CH2:5][C:4]([OH:24])=[O:3])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:18])([CH3:23])([CH3:21])[CH3:22]Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A solution of (E)-tert-butyl 3-(3-ethoxy-3-oxoprop-1-enyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (8.7 g, 26.3 mmol) and Pd/C (cat) in ethanol (150 mL, 0.18 M) was evacuated to remove air then treated with hydrogen via a balloon. After stirring for 4 h, 3 M sodium hydroxide was added to adjust the solution to pH 11 and the mixture was stirred overnight. The resulting solution was filtered, concentrated, acidified to pH 2 and extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered and concentrated to give 3-(2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinolin-3-yl)propanoic acid as a yellow oil (7.7 g, 96%). ESI MS found for C17H23NO4 m/z [328.4 (M+23)]. The crude product was used without further purification.