Water → 2-(N-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinolin-5-yl)carbonyl-4-chloro-aniline

HRID 275880

Reaktionsgleichung

[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2Br)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(OC)[C:21](=[O:30])[C:22]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=1[NH2:29].C([Li])CCC.O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[C:21]([C:22]2[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=2[NH2:29])=[O:30])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

In tetrahydrofuran (15 ml) were dissolved N-tert-butoxycarbonyl-5-bromo-1,2,3,4-tetrahydroisoquinoline (0.9 g) and N-methyl-N-methyloxy-2-amino-5-chlorobenzamide (0.68 g). The solution was cooled to −78° C., to which was added dropwise, while stirring, n-butyl lithium (1.6 mol, hexane solution) (9 ml) over 30 minutes. To the reaction mixture was added water (50 ml) to decompose, followed by extraction with ethyl acetate (80 ml). The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by means of a silica gel column chromatography to give 2-(N-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinolin-5-yl)carbonyl-4-chloro-aniline (0.26 g) as a yellow crystalline product. m.p.: 159-160° C.

Aufarbeitung

additionwas added dropwise
extractionfollowed by extraction with ethyl acetate (80 ml)
washThe organic layer was washed with water
dry with materialdried over anhydrous sodium sulfate
distillationThe solvent was distilled off
customthe residue was purified by means of a silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-8782a5f5ade44b199338805ded6a5427
Quelldatensatz: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06352982B1

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