tert-butyl 6-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Base Information

• Chemical Name: tert-butyl 6-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
• CAS No.: 622867-52-1
• Molecular Formula: C15H21NO3
• Molecular Weight: 263.337
• Mol file: 622867-52-1.mol

Synonyms:tert-butyl 6-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Chemical Property of tert-butyl 6-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Chemical Property:

• Boiling Point: 403.7±45.0 °C(Predicted)
• PKA: 14.44±0.10(Predicted)
• PSA: 49.77000
• Density: 1.153±0.06 g/cm3(Predicted)
• LogP: 2.41000
• Storage Temp.: 2-8°C

Purity/Quality:

95-99% ^*data from raw suppliers

N-Boc-6-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-Boc-6-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline is an intermediate used to prepare phosphonate-substituted HIV protease inhibitors for treatment of AIDS and other viral infections. It is also used in the synthesis of immunosuppressant heterocyclic compdounds for treating or preventing diseases assocd. with EDG receptor mediated signal transduction.

Technology Process of tert-butyl 6-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

There total 6 articles about tert-butyl 6-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 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: 99.7%

2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid (170097-67-3) → 6-hydroxymethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (622867-52-1)

Guidance literature:

2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid; With borane-THF; In tetrahydrofuran; at 25 ℃; for 16h; Inert atmosphere;

With sodium carbonate; In tetrahydrofuran; water; for 0.25h;

Reference yield:

3,4-Dihydro-1H-isoquinoline-2.6-dicarboxylic acid 2-tert-butyl ester-6-methyl ester (170097-66-2) → 6-hydroxymethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (622867-52-1)

Guidance literature:

With methanol; lithium borohydride; In tetrahydrofuran; for 2h; Reflux; Inert atmosphere;

Reference yield:

N-t-butoxycarbonyl 1,2,3,4-tetrahydroisoquinoline-6-formaldehyde (371222-37-6) → 6-hydroxymethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (622867-52-1)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 - 20 ℃; for 1h;

upstream raw materials:

3,4-Dihydro-1H-isoquinoline-2.6-dicarboxylic acid 2-tert-butyl ester-6-methyl ester

2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid

N-t-butoxycarbonyl 1,2,3,4-tetrahydroisoquinoline-6-formaldehyde

6-bromo-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline

Downstream raw materials:

6-bromomethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

C₃₁H₂₉F₃N₄O₄

C₃₄H₃₈N₄O₅

Refernces

• 1、 -. "SUBSTITUTED TETRAHYDROISOQUINOLINE COMPOUNDS USEFUL AS GPR120 AGONISTS". Page/Page column 137. . Retrieved 2017/12/29.
• 2、 -. "SUBSTITUTED PYRIDINES AS INHIBITORS OF DNMT1". Page/Page column 643-644. . Retrieved 2018/01/20.