219943-51-8

Basic information

• Product Name: (R)-4-bromo-α-N-trityltryptophan
• Synonyms: (R)-4-bromo-α-N-trityltryptophan
• CAS NO: 219943-51-8
• Molecular Weight: 525.445
• Mol File: 219943-51-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (R)-4-bromo-α-N-trityltryptophan(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-bromo-α-N-trityltryptophan(219943-51-8)
• EPA Substance Registry System: (R)-4-bromo-α-N-trityltryptophan(219943-51-8)

Safety Data

• Hazardous Substances Data: 219943-51-8(Hazardous Substances Data)

Upstream product

• 219943-61-0 (R)-4-bromotryptophan 
• 219943-45-0 4-Bromo-3-[(R)-3-methoxymethoxy-2-(9-phenyl-9H-fluoren-9-ylamino)-propyl]-indole-1-carboxylic acid tert-butyl ester 
• 219943-49-4 (R)-4-bromo-1-(tert-butyloxycarbonyl)-α-N-(9-phenyl-9-fluorenyl)tryptophan 
• 219943-46-1 4-Bromo-3-[(R)-3-hydroxy-2-(9-phenyl-9H-fluoren-9-ylamino)-propyl]-indole-1-carboxylic acid tert-butyl ester 
• 219943-47-2 4-Bromo-3-[(R)-3-oxo-2-(9-phenyl-9H-fluoren-9-ylamino)-propyl]-indole-1-carboxylic acid tert-butyl ester 
• 219943-44-9 [(R)-2-(4-Bromo-1H-indol-3-yl)-1-methoxymethoxymethyl-ethyl]-(9-phenyl-9H-fluoren-9-yl)-amine 
• 219943-38-1 3,4-Dibromo-indole-1-carboxylic acid tert-butyl ester 
• 219943-37-0 3,4-dibromo-1H-indole 
• 76-83-5 trityl chloride 
• 52488-36-5 4-bromo-1H-indole 
• 219943-53-0 (R)-4-bromo-α-N-trityltryptophan methyl ester 
• 219943-50-7 (R)-4-bromo-α-N-trityltryptophan trityl ester 

Downstream Products

• 219943-53-0 (R)-4-bromo-α-N-trityltryptophan methyl ester 
• 219943-55-2 (R)-4-(Trityl-amino)-3,4-dihydro-1H-benzo[cd]indol-5-one 
• 219943-56-3 (R)-5-Oxo-4-(trityl-amino)-4,5-dihydro-3H-benzo[cd]indole-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Enantiospecific synthesis of (r)-4-amino-5-oxo-1,3,4,5- tetrahydrobenz[cd]indole, an advanced intermediate containing the tricyclic core of the ergots

We report a new strategy for the enantiospecific synthesis of (R)-4- amino-5-oxo-1,3,4,5-tetrahydrobenz[cd]indole. This compound is an advanced intermediate which contains the tricyclic core of many of the tetracyclic ergot alkaloids. Our method involves the initial synthesis of D-4- bromotryptophan from the coupling of an indolyllithium species with a masked serinal. The α-amino position was protected with an N-trityl group, ensuring the enantiomeric integrity of this position during the ensuing organometallic cyclization reaction. Stabilization of the tricycle was accomplished by protecting the indole nitrogen with a BOC group or by reducing the α-amino ketone to the corresponding β-amino alcohol.