Butanedioic acid, 2,3-bis(benzoyloxy)-, (2S,3S)-, compd. with ethyl (11bS)-2-amino-1,6,7,11b-tetrahydro-9,10-dimethoxy-4H-benzo[a]quinolizine-3-carboxylate (1:1)

Base Information

• Chemical Name: Butanedioic acid, 2,3-bis(benzoyloxy)-, (2S,3S)-, compd. with ethyl (11bS)-2-amino-1,6,7,11b-tetrahydro-9,10-dimethoxy-4H-benzo[a]quinolizine-3-carboxylate (1:1)
• CAS No.: 1012065-72-3
• Molecular Formula: C18H24N2O4.C18H14O8
• Molecular Weight: 690.704
• Mol file: 1012065-72-3.mol

Synonyms:Butanedioic acid, 2,3-bis(benzoyloxy)-, (2S,3S)-, coMpd. with ethyl (11bS)-2-aMino-1,6,7,11b-tetrahydro-9,10-diMethoxy-4H-benzo[a]quinolizine-3-carboxylate (1:1)

Chemical Property of Butanedioic acid, 2,3-bis(benzoyloxy)-, (2S,3S)-, compd. with ethyl (11bS)-2-amino-1,6,7,11b-tetrahydro-9,10-dimethoxy-4H-benzo[a]quinolizine-3-carboxylate (1:1)

Chemical Property:

• PSA: 201.22000
• LogP: 4.02760

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Butanedioic acid, 2,3-bis(benzoyloxy)-, (2S,3S)-, compd. with ethyl (11bS)-2-amino-1,6,7,11b-tetrahydro-9,10-dimethoxy-4H-benzo[a]quinolizine-3-carboxylate (1:1)

There total 6 articles about Butanedioic acid, 2,3-bis(benzoyloxy)-, (2S,3S)-, compd. with ethyl (11bS)-2-amino-1,6,7,11b-tetrahydro-9,10-dimethoxy-4H-benzo[a]quinolizine-3-carboxylate (1:1) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 45.1%

(+/-)-2-amino-9,10-dimethoxy-1,6,7,11b-tetrahydro-4H-pyrido[2,1-a]isoquinoline-3-carboxylic acid ethyl ester (557101-39-0) + (+/-)-2,3-O-dibenzoyltartaric acid (2743-38-6,17026-42-5,22333-70-6,100632-52-8,111955-48-7) → (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 (1012065-72-3)

Guidance literature:

In ethanol; water; at 20 - 50 ℃; for 16.5h; Resolution of racemate;

Reference yield: 45.1%

(+/-)-2-amino-9,10-dimethoxy-1,6,7,11b-tetrahydro-4H-pyrido[2,1-a]isoquinoline-3-carboxylic acid ethyl ester (557101-39-0) + O,O'-dibenzoyl-D-tartaric acid (17026-42-5) → (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 (1012065-72-3) + (R)-2-amino-9,10-dimethoxy-1,6,7,11b-tetrahydro-4H-pyrido[2,1-a]isoquinoline-3-carboxylic acid ethyl ester

Guidance literature:

In ethanol; water; at 20 - 50 ℃; for 16.5h; Purification / work up; Resolution of racemate;

Reference yield:

3-oxo-glutaric acid monoethyl ester (5526-36-3) → (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 (1012065-72-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium acetate / ethanol; water / 1.5 h / 20 - 25 °C / Large scale reaction

1.2: 0 - 5 °C / Large scale reaction

2.1: sodium acetate / methanol; water / 20 - 25 °C / Large scale reaction

3.1: ammonium acetate / methanol / 45 - 50 °C / Large scale reaction

4.1: methanol; ethanol / 24 h / 60 °C / Large scale reaction

With ammonium acetate; sodium acetate; In methanol; ethanol; water; 2.1: Mannich cyclization;

DOI:c

upstream raw materials:

(+/-)-2-amino-9,10-dimethoxy-1,6,7,11b-tetrahydro-4H-pyrido[2,1-a]isoquinoline-3-carboxylic acid ethyl ester

O,O'-dibenzoyl-D-tartaric acid

(+/-)-2,3-O-dibenzoyltartaric acid

3-oxo-glutaric acid monoethyl ester

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF PYRIDO [2,1-a] ISOQUINOLINE DERIVATIVES COMPRISING OPTICAL RESOLUTION OF AN ENAMINE". Page/Page column 10. . Retrieved 2008/06/13.