6-(2-(1H-tetrazol-5-yl)ethyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylic acid

Base Information

• Chemical Name: 6-(2-(1H-tetrazol-5-yl)ethyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylic acid
• CAS No.: 150131-78-5
• Molecular Weight: 0
• Mol file: 150131-78-5.mol

Synonyms:6-(2-(1H-tetrazol-5-yl)ethyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylic acid

Chemical Property of 6-(2-(1H-tetrazol-5-yl)ethyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 6E-12mmHg at 25°C
• Boiling Point: 527.3°C at 760 mmHg
• Flash Point: 272.7°C
• Density: 1.252g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(2-(1H-tetrazol-5-yl)ethyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylic acid

There total 35 articles about 6-(2-(1H-tetrazol-5-yl)ethyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylic acid 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:

ethyl (3S,4aR,8aR)-6-oxo-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate → (3S,4aR,6R,8aR)-6-[2-(1H-tatrazol-5-yl)ethyl]decahydroisoquinoline-3-carboxylic acid (154652-83-2,150131-78-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / NaN(SiMe₃)2 / tetrahydrofuran

2: 1.) BH₃*SMe₂, 2.) NaOH, H₂O₂ / 1.) THF, 0 deg C

With sodium hydroxide; dimethylsulfide borane complex; dihydrogen peroxide; sodium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1080/10426509608545152

Reference yield:

Ethyl (3S,4aR,8aR)-6-methylidene-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate (157006-68-3) → (3S,4aR,6R,8aR)-6-[2-(1H-tatrazol-5-yl)ethyl]decahydroisoquinoline-3-carboxylic acid (154652-83-2,150131-78-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) BH₃*SMe₂, 2.) NaOH, H₂O₂ / 1.) THF, 0 deg C

With sodium hydroxide; dimethylsulfide borane complex; dihydrogen peroxide;

DOI:10.1080/10426509608545152

Reference yield:

(3S,4aS,8aR)-6-Oxo-octahydro-isoquinoline-2,3-dicarboxylic acid 3-ethyl ester 2-methyl ester (128073-42-7,134388-86-6,134388-92-4,134389-01-8,134389-03-0,134389-04-1) → (3SR,4aRS,6RS,8aRS)-6-(2-(1H-Tetrazol-5-yl)ethyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylic acid (150131-78-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, 0 deg C, 15 min, 2.) THF, 0 deg C

2: 1.) borane methyl sulfide, 2.) 3 N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 2 h; r.t., 2.5 h, 2.) EtOH, 0 deg C, 30 min; r.t., 2 h

3: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) -78 deg C, 45 min

4: 95 percent / NaH / tetrahydrofuran / 1.) r.t., 30 min, 2.) 0 deg C, 45 min

With sodium hydroxide; oxalyl dichloride; dimethylsulfide borane complex; dihydrogen peroxide; sodium hexamethyldisilazane; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran;

DOI:10.1021/jo00104a051

upstream raw materials:

Ethyl (3S,4aR,6S,8aR)-6-(2-cyanoethenyl)-2-carbomethoxy-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate

methanol

diethyl 1-cyanomethylphosphonate

Ethyl (3S,4aR,6S,8aR)-6-(hydroxymethyl)-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate

Refernces

• 1、 Ornstein, Paul L.,Arnold, M. Brian,Allen, Nancy K.,Schoepp, Darryle D.. "Synthesis and characterization of phosphonic acid-substituted amino acids as excitatory amino acid receptor antagonists". . p. 309 - 312. Retrieved 2007/10/03.