229496-33-7

Upstream product

• 19472-74-3 2-(2-bromophenyl)acetonitrile 
• 501-53-1 benzyl chloroformate 
• 65185-58-2 2-(2-bromophenyl)ethanamine 

Downstream Products

• 1273547-06-0 (3S)-(E)-N-Cbz-N-[2-[2-(3-hydroxy-1-butenyl)phenyl]ethyl]amine 
• 1307795-03-4 N-(2-{4'-[(1R,3'S)-5-fluoro-6-methoxy-3-oxo-3H-spiro[2-benzofuran-1,4'-piperidin]-3'-yl]-3'-methyl-2-biphenylyl}ethyl)-2-hydroxyacetamide 
• 1307795-94-3 tert-butyl (1R,3'S)-5-fluoro-3'-{2'-[2-(glycoloylamino)ethyl]-3-methyl-4-biphenylyl}-6-methoxy-3-oxo-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate 
• 1307795-01-2 N-(2-{4'-[(1R,3'S)-5,6-difluoro-3-oxo-3H-spiro[2-benzofuran-1,4'-piperidin]-3'-yl]-3'-methyl-2-biphenylyl}ethyl)-2-hydroxyacetamide 
• 1307795-92-1 tert-butyl (1R,3'S)-5,6-difluoro-3'-{2'-[2-(glycoloylamino)ethyl]-3-methyl-4-biphenylyl}-3-oxo-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate 
• 1307795-91-0 tert-butyl (1R,3'S)-3'-[2'-(2-{[(acetyloxy)acetyl]amino}ethyl)-3-methyl-4-biphenylyl]-5,6-difluoro-3-oxo-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate 
• 1307794-99-5 methyl (2-{4'-[(1R,3'S)-5,6-difluoro-3-oxo-3H-spiro[2-benzofuran-1,4'-piperidin]-3'-yl]-3'-methyl-2-biphenylyl}ethyl)carbamate hydrochloride 
• 1307795-89-6 tert-butyl (1R,3'S)-5,6-difluoro-3'-(2'-{2-[(methoxycarbonyl)amino]ethyl}-3-methyl-4-biphenylyl)-3-oxo-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate 
• 1307795-88-5 tert-butyl (1R,3'S)-5,6-difluoro-3'-{3-methyl-2'-[2-(propionylamino)ethyl]-4-biphenylyl}-3-oxo-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate 
• 1307794-95-1 N-(2-{4'-[(1R,3'S)-5,6-difluoro-3-oxo-3H-spiro(2-benzofuran-1,4'-piperidin)-3'-yl]-3'-methyl-2-biphenylyl}ethyl)acetamide hydrochloride 
• 1307795-85-2 tert-butyl (1R,3'S)-3'-{2'-[2-(acetylamino)ethyl]-3-methyl-4-biphenylyl}-5,6-difluoro-3-oxo-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate 
• 1307795-83-0 tert-butyl (1R,3'S)-3'-[2'-(2-aminoethyl)-3-methyl-4-biphenylyl]-5,6-difluoro-3-oxo-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate 
• 1307795-80-7 tert-butyl (1R,3'S)-3'-[2'-(2-{[(benzyloxy)carbonyl]amino}ethyl)-3-methyl-4-biphenylyl]-5,6-difluoro-3-oxo-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate 
• 1247090-07-8 benzyl {2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl}carbamate 

Relevant academic research and scientific papers

Preparation method of (S)-5-bromo-1, 2, 3, 4-tetrahydro-N-Boc-isoquinoline-1-carboxylic acid

The invention discloses a preparation method for synthesizing (S)-5-bromo-1, 2, 3, 4-tetrahydro-N-Boc-isoquinoline-1-carboxylic acid, and belongs to the technical field of medical intermediates. The method comprises the following steps: reacting o-bromophenylethylamine serving as a raw material with benzyl chloroformate in an alkaline environment to obtain benzyl o-bromophenylethylamine formate; then carrying out cyclization reaction with glyoxylic acid under the catalysis of acid; then carrying out palladium-carbon catalytic hydrogenation to remove protection, so as to obtain 5-bromo-1, 2, 3, 4-tetrahydroisoquinoline-1-carboxylic acid; finally, obtaining the (S)-5-bromo-1, 2, 3, 4-tetrahydro-N-Boc-isoquinoline-1-carboxylic acid through induced resolution and Boc protection. The method is simple, convenient and stable in process operation, high in yield, environmentally friendly, cheap and easily available in raw materials and beneficial to industrial production.

Synthesis of chiral 1-substituted tetrahydroisoquinolines by the intramolecular 1,3-chirality transfer reaction catalyzed by Bi(OTf)3

The intramolecular 1,3-chirality transfer reaction of chiral amino alcohols 1 with 99% ee was developed to construct chiral 1-substituted tetrahydroisoquinoline 2. Bi(OTf)3 (10 mol %)-catalyzed cyclization of 1 (R = H) afforded (S)-1-(E)-propenyl tetrahydroisoquinoline 2 (R = H) in 83% yield with a ratio of 98:2. The stereochemistry at the newly formed chiral center was produced by a syn SN2′-type process. In this reaction, the substituent on the benzene ring of 1 significantly affected the reactivities and selectivities. A plausible reaction mechanism was proposed.

A mild inter- and intramolecular amination of aryl halides with a combination of CuI and CsOAc

A unique combination of CuI and CsOAc was found to catalyze aryl amination under mild conditions. The reaction takes place at room temperature or at 90 °C with broad functional group compatibility. The intramolecular reaction was able to form five-, six-, and seven-membered rings with various protecting groups on the nitrogen atom. The scope of the intermolecular amination, as well as its applications to unsymmetrical N,N′-dialkylated phenylenediamines, was investigated.