110969-45-4

Usage

InChI:InChI=1/C13H19NO2/c1-5-10-8-6-7-9-11(10)14-12(15)16-13(2,3)4/h6-9H,5H2,1-4H3,(H,14,15)

Upstream product

• 578-54-1 ortho-ethylaniline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 109774-64-3 Acetyl-(4-tert-butyl-phenyl)-carbamic acid tert-butyl ester 

Downstream Products

• 1035225-97-8 C₂₀H₃₁NO₃ 
• 314773-77-8 tert-butyl (2-acetylphenyl)carbamate 
• 1301630-30-7 1,1-dimethylethyl N-(2-ethylphenyl)-N-methyl-carbamate 
• 1301630-31-8 1,1-dimethylethyl N-(2-ethylphenyl)-N-[(methylthio)methyl]carbamate 
• 1301630-32-9 C₁₅H₂₃NO₂S 
• 1504-06-9 3-methylindolin-2-one 

Relevant academic research and scientific papers

Preparation of indoles and oxindoles from N-(tert-butoxycarbonyl)-2-alkylanilines

Treatment of dilithiated N-(tert-butoxycarbonyl)anilines 1 with dimethylformamide or carbon dioxide furnishes intermediates 3, 5, that are easily converted to N-(tert-butoxycarbonyl)indoles 4 and oxindoles (indol-2(3H)-ones, 7), respectively. Condensation of dilithiated 1 with N-methoxy-N-methylamides provides ketones 9 which are cyclized upon trifluoroacetic acid treatment to either 2-substituted 1-(tert-butoxycarbonyl)indoles 10 or 2-substituted indoles 11 depending on the reaction time. This general methodology has been applied to efficient synthesis of 1,2-alkyl-bridged indoles 12, 1,3,4,5-tetrahydrobenz[c,d]indole (16), 2a,3,4,5-tetrahydrobenz[c,d]indol-2(1H)-one (18), and 1-(tert-butoxycarbonyl)1H-pyrrolo[2,3-b]pyridine (21).

Selective Cleavage of Boc-acylamides. A Novel Approach to Deacylation of Carboxamides

Boc (tert-butoxycarbonyl) derivatives were recently prepared from various amides.This paper describes some of their properties with particular attention to mild amide cleavage.Boc-protected carboxamides were cleaved by aminolysis with complete selectivity to give the corresponding tert-butyl carbamates.The amines used ranged from hydrazine to morpholine, but for preparative purposes 2-diethylaminoethylamine was preferred.A simple two-step one-pot procedure for tert-butoxycarbonylation followed by aminolysis was developed which could be used for removal of formyl, ace tyl, and benzoyl groups.In extreme cases, there derivatives were cleaved by alcoholysis.Upon addition of bases such as N,N,N',N'-tetramethylguanidine (TMS) this reaction became very fast.TMS-catalysed methanolysis gave 98percent cleavage in 30 min or less in two preparative experiments.