2-BOC-6-HYDROXY-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-1-CARBOXYLIC ACID

Base Information

• Chemical Name: 2-BOC-6-HYDROXY-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-1-CARBOXYLIC ACID
• CAS No.: 362492-00-0
• Molecular Formula: C15H19NO5
• Molecular Weight: 293.32
• Hs Code.: 2933499090
• Mol file: 362492-00-0.mol

Synonyms:2-(tert-butoxycarbonyl)-6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid;1,2(1H)-Isoquinolinedicarboxylic acid, 3,4-dihydro-6-hydroxy-, 2-(1,1-dimethylethyl) ester;

Chemical Property of 2-BOC-6-HYDROXY-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-1-CARBOXYLIC ACID

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.579
• Boiling Point: 497.928 °C at 760 mmHg
• Flash Point: 254.938 °C
• PSA: 87.07000
• Density: 1.303 g/cm³
• LogP: 2.24900

Purity/Quality:

98%min ^*data from raw suppliers

2-Boc-6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-BOC-6-HYDROXY-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-1-CARBOXYLIC ACID

There total 10 articles about 2-BOC-6-HYDROXY-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-1-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: 97.5%

methyl N-(tert-butyloxycarbonyl)-6-hydroxy-3,4-dihydro-1H-isoquinoline-1-carboxylate (350014-19-6) → 2-(tert-butoxycarbonyl)-6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (362492-00-0)

Guidance literature:

methyl N-(tert-butyloxycarbonyl)-6-hydroxy-3,4-dihydro-1H-isoquinoline-1-carboxylate; With sodium hydroxide; water; In tetrahydrofuran; methanol; at 20 - 60 ℃;

With hydrogenchloride; In water; pH=~ 3;

Reference yield:

ethyl (1SR)-6-hydroxy-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylate (128073-49-4) → 2-(tert-butoxycarbonyl)-6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (362492-00-0)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; ethanol; water; at 20 ℃;

Reference yield:

m-tyramine (588-05-6) → 2-(tert-butoxycarbonyl)-6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (362492-00-0)

Guidance literature:

Multi-step reaction with 4 steps

1: aq. HCl

2: TMSiCl

3: Et₃N

4: NaOH

With hydrogenchloride; sodium hydroxide; chloro-trimethyl-silane; triethylamine;

DOI:10.1016/j.bmcl.2005.02.040

upstream raw materials:

methyl N-(tert-butyloxycarbonyl)-6-hydroxy-3,4-dihydro-1H-isoquinoline-1-carboxylate

m-tyramine

rac-6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

1,2,3,4-Tetrahydro-6-hydroxy-1-isoquinolinecarboxylic acid methyl ester

Downstream raw materials:

C₂₈H₃₉N₃O₃

C₂₉H₄₁N₃O₄

C₂₉H₄₁N₃O₄

Refernces

• 1、 Li, James J.,Wang, Haixia,Qu, Fucheng,Musial, Christa,Tino, Joseph A.,Robl, Jeffrey A.,Slusarchyk, Dorothy,Golla, Rajasree,Seethala, Ramakrishna,Dickinson, Kenneth,Giupponi, Leah,Grover, Gary,Sleph, Paul,Flynn, Neil,Murphy, Brian J.,Gordon, David,Kung, Melissa,Stoffel, Robert. "Tetrahydroisoquinoline 1-carboxamides as growth hormone secretagogues". . p. 1799 - 1802. Retrieved 2007/10/03.