557101-39-0

Basic information

• Product Name: ethyl 2-amino-9,10-dimethoxy-4,6,7,11b-tetrahydro-1H-benzo[a]quinolizine-3-carboxylate
• CAS NO: 557101-39-0
• Molecular Formula: C₁₈H₂₄N₂O₄
• Molecular Weight: 332.39
• Mol File: 557101-39-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 484.7°C at 760 mmHg
• Flash Point: 246.9°C
• Density: 1.24g/cm³
• Vapor Pressure: 1.5E-09mmHg at 25°C
• Refractive Index: 1.593
• CAS DataBase Reference: ethyl 2-amino-9,10-dimethoxy-4,6,7,11b-tetrahydro-1H-benzo[a]quinolizine-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-amino-9,10-dimethoxy-4,6,7,11b-tetrahydro-1H-benzo[a]quinolizine-3-carboxylate(557101-39-0)
• EPA Substance Registry System: ethyl 2-amino-9,10-dimethoxy-4,6,7,11b-tetrahydro-1H-benzo[a]quinolizine-3-carboxylate(557101-39-0)

Safety Data

• Hazardous Substances Data: 557101-39-0(Hazardous Substances Data)

Upstream product

• 5526-36-3 3-oxo-glutaric acid monoethyl ester 
• 50-00-0 formaldehyd 
• 52244-03-8 ethyl 3-(1-(2-ethoxy-2-oxoethyl)-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)propanoate 
• 5911-33-1 ethyl 9,10-dimethoxy-2-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline-3-carboxylate 

Downstream Products

• 1012065-72-3 (S)-2-amino-9,10-dimethoxy-1,6,7,11b-tetrahydro-4H-pyrido[2,1-a]isoquinoline-3-carboxylic acid ethyl ester, (S,S)-2,3-bisbenzoyloxysuccinic acid salt 
• 1012065-68-7 (S)-2-amino-9,10-dimethoxy-1,6,7,11b-tetrahydro-4H-pyrido[2,1-a]isoquinoline-3-carboxylic acid ethyl ester (2S,3S)-bis-benzyloxy-N,N-dimethyl-succinamic acid salt 

Relevant articles and documents

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A short and high-yielding synthesis of carmegliptin (1) suitable for large-scale production is reported. The tricyclic core was assembled efficiently by a decarboxylative Mannich addition-Mannich cyclization sequence. Subsequent crystallization-induced dynamic resolution of enamine 7 using (S,S)-dibenzoyltartaric acid was followed by diastereoselective enamine reduction to give the fully functionalized tricyclic core with its three stereogenic centers. The C-3 nitrogen was introduced by Hofmann rearrangement of amide 28, and the resulting amine 10 was coupled with (S)-fluoromethyl lactone 31. Following cyclization to lactam 13 and amine deprotection, 1 was obtained in 27-31% overall yield with six isolated intermediates.

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