benzyl (3S)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride

Base Information

• Chemical Name: benzyl (3S)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride
• CAS No.: 103733-32-0
• Molecular Formula: C19H21NO4.HCl
• Molecular Weight: 363.841
• DSSTox Substance ID: DTXSID20516138
• Mol file: 103733-32-0.mol

Synonyms:103733-32-0;benzyl (3S)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride;benzyl (3S)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate;hydrochloride;(3S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-3-isoquinolinecarboxylic Acid Phenylmethyl Ester Hydrochloride;GQDUPSRSUSSQLG-NTISSMGPSA-N;DTXSID20516138;AKOS015950919;(S)-1,2,3,4-tetrahydro-6,7-dimethoxy-3-isoquinolinecarboxylic acid benzyl ester, hydrochloride;Benzyl (3S)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate--hydrogen chloride (1/1)

Chemical Property of benzyl (3S)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride

Chemical Property:

• PSA: 56.79000
• LogP: 3.59230
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 363.1237359
• Heavy Atom Count: 25
• Complexity: 410

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2CNC(CC2=C1)C(=O)OCC3=CC=CC=C3)OC.Cl
• Isomeric SMILES: COC1=C(C=C2CN[C@@H](CC2=C1)C(=O)OCC3=CC=CC=C3)OC.Cl

Technology Process of benzyl (3S)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride

There total 3 articles about benzyl (3S)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride 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: 99.0%

(S)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-(tert-butyloxycarbonyl)-3-isoquinolinecarboxylic acid benzyl ester (617699-49-7) → (S)-1,2,3,4-tetrahydro-6,7-dimethoxy-3-isoquinolinecarboxylic acid, phenylmethylester, hydrochloride (103733-32-0)

Guidance literature:

With hydrogenchloride; In ethyl acetate; isopropyl alcohol; toluene; at 15 - 40 ℃; for 5 - 6h; Product distribution / selectivity;

Reference yield: 90.2%

(S)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-(tert-butyloxycarbonyl)-3-isoquinolinecarboxylic acid (358627-67-5) + benzyl alcohol (100-51-6,185532-71-2) → (S)-1,2,3,4-tetrahydro-6,7-dimethoxy-3-isoquinolinecarboxylic acid, phenylmethylester, hydrochloride (103733-32-0)

Guidance literature:

(S)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-(tert-butyloxycarbonyl)-3-isoquinolinecarboxylic acid; benzyl alcohol; toluene-4-sulfonic acid; In toluene; Heating / reflux; Dean-Stark apparatus;

With hydrogenchloride; In tert-butyl methyl ether; isopropyl alcohol; toluene; at 20 ℃; Product distribution / selectivity;

Reference yield:

(S)‐6,7‐dimethoxy‐1,2,3,4-tetrahydroisoquinoline‐3‐carboxylate hydrochloride (82586-62-7) + benzyl alcohol (100-51-6,185532-71-2) → (S)-1,2,3,4-tetrahydro-6,7-dimethoxy-3-isoquinolinecarboxylic acid, phenylmethylester, hydrochloride (103733-32-0)

Guidance literature:

With hydrogenchloride; for 72h; Ambient temperature;

DOI:10.1021/jm00160a026

upstream raw materials:

(S)‐6,7‐dimethoxy‐1,2,3,4-tetrahydroisoquinoline‐3‐carboxylate hydrochloride

benzyl alcohol

(S)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-(tert-butyloxycarbonyl)-3-isoquinolinecarboxylic acid

(S)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-(tert-butyloxycarbonyl)-3-isoquinolinecarboxylic acid benzyl ester

Refernces

• 1、 Klutchko,Blankley,Fleming,Hinkley,Werner,Nordin,Holmes,Hoefle,Cohen,Essenburg. "Synthesis of novel angiotensin converting enzyme inhibitor quinapril and related compounds. A divergence of structure-activity relationships for non-sulfhydryl and sulfhydryl types". . p. 1953 - 1961. Retrieved 2007/10/02.