1229616-22-1

Basic information

• Product Name: (3R,11aR)-3-phenyl-2,3,11,11a-tetrahydro[1,3]oxazolo-[3,2-b][2]benzazepin-5(10H)-one
• Synonyms: (3R,11aR)-3-phenyl-2,3,11,11a-tetrahydro[1,3]oxazolo-[3,2-b][2]benzazepin-5(10H)-one
• CAS NO: 1229616-22-1
• Molecular Weight: 279.338
• Mol File: 1229616-22-1.mol

Chemical Properties

• CAS DataBase Reference: (3R,11aR)-3-phenyl-2,3,11,11a-tetrahydro[1,3]oxazolo-[3,2-b][2]benzazepin-5(10H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,11aR)-3-phenyl-2,3,11,11a-tetrahydro[1,3]oxazolo-[3,2-b][2]benzazepin-5(10H)-one(1229616-22-1)
• EPA Substance Registry System: (3R,11aR)-3-phenyl-2,3,11,11a-tetrahydro[1,3]oxazolo-[3,2-b][2]benzazepin-5(10H)-one(1229616-22-1)

Safety Data

• Hazardous Substances Data: 1229616-22-1(Hazardous Substances Data)

Upstream product

• 1229616-17-4 2-[2-(1,3-dioxolan-2-yl)ethyl]-N-[(1R)-2-hydroxy-1-phenylethyl]benzamide 
• 583-55-1 1-Bromo-2-iodobenzene 
• 544708-10-3 2-[2-(2-bromophenyl)ethyl]-1,3-dioxolane 
• 1229616-16-3 2-[2-(1,3-dioxolan-2-yl)ethyl]benzoic acid 
• 107408-16-2 3-(o-bromophenyl)propanal 

Downstream Products

• 1229616-18-5 (3S)-2-[(1R)-2-hydroxy-1-phenylethyl]-3-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-2-benzazepin-1-one 
• 1229616-21-0 (2R)-2-phenyl-2-[(3S)-3-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1H-2-benzazepin-2-yl]ethanol 

Relevant articles and documents

Asymmetric synthesis of 3-substituted tetrahydro-2-benzazepines

The enantiomerically and diastereomerically pure tricyclic oxazolidine cis-10 was prepared in a five step synthesis starting with 1-bromo-2-iodobenzene. Me3SiCN and allylSiMe3 reacted with cis-10 in the presence of TiCl4 to form the nitrile (3S)-11 and the allyl derivative (3S)-12 with high diastereoselectivity. The hydrogenolytic removal of the chiral auxiliary failed, since the endocyclic benzyl-N-bond was cleaved simultaneously. Therefore the N-(hydroxyethyl)amide of (3S)-12 was transformed into the enamide 27, which was hydrolyzed to afford the secondary amide 28. The enamide strategy to remove the chiral auxiliary from (3S)-11 led to complete racemization due to fast deprotonation in α-position of the cyano moiety. Two pairs of enantiomers 30a-b/ent-30a-b with prototypical σ substituents at the N-atom were prepared. The low σ1 affinity of the tetrahydro-2-benzazepines (ent-30b, Ki = 407 nM) is attributed to the short distance between the two lipophilic aromatic moieties.

(3R,11aR)-3-Phenyl-2,3,11,11a-tetrahydro-[1,3]oxazolo[3,2-b]-[2]benzazepin-5(10H)-one as a chiral building block for the asymmetric synthesis of 3-substituted 2-benzazepines

A five-step synthesis of the chiral building block cis-2 is described. Key steps in the synthesis were a Heck reaction of 1-bromo-2-iodobenzene with allyl alcohol, the introduction of a carboxy group after Br/Li-exchange, and the diastereoselective format