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

참여 물질

역할	이름	HCID	투입량
반응물	Water	HCID 962	—
반응물	tert-Butyl 5-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate	HCID 18315369	—
반응물	2-amino-5-chloro-N-methoxy-N-methylbenzamide	HCID 22226605	—
반응물	Butyllithium	HCID 178418339	—
용매	Tetrahydrofuran	HCID 8028	—
생성물	2-(N-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinolin-5-yl)carbonyl-4-chloro-aniline	HCID 18315344	23.3%

반응 조건

온도	-78 °C

반응 단계

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.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US06352982B1
출처 데이터셋	uspto-grants-2002_03
ORD ID	ord-8782a5f5ade44b199338805ded6a5427
출처 메모	uspto-grants-2002_03