tert-butyl 6-hydroxy-5-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Base Information

• Chemical Name: tert-butyl 6-hydroxy-5-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
• CAS No.: 1165923-89-6
• Molecular Formula: C15H21NO3
• Molecular Weight: 263.33
• Hs Code.: 2933499090
• Mol file: 1165923-89-6.mol

Synonyms:tert-butyl 6-hydroxy-5-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Chemical Property of tert-butyl 6-hydroxy-5-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Chemical Property:

• PSA: 49.77000
• LogP: 2.93170

Purity/Quality:

98%min ^*data from raw suppliers

tert-Butyl6-Hydroxy-5-methyl-3,4-dihydroisoquinoline-2(1h)-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tert-butyl 6-hydroxy-5-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

There total 23 articles about tert-butyl 6-hydroxy-5-methyl-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: 83.1%

Trimethylboroxine (823-96-1) + 5-bromo-6-hydroxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tertbutyl ester → 1,1-dimethylethyl 6-hydroxy-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (1165923-89-6)

Guidance literature:

With palladium diacetate; potassium carbonate; ruphos; In water; toluene; at 90 ℃; for 12h; Sealed tube; Inert atmosphere;

Reference yield: 55.0%

1,1-dimethylethyl 5-methyl-6-oxo-3,4,6,7,8,8a-hexahydro-2(1H)-isoquinolinecarboxylate (1258440-70-8) → 1,1-dimethylethyl 6-hydroxy-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (1165923-89-6)

Guidance literature:

1,1-dimethylethyl 5-methyl-6-oxo-3,4,6,7,8,8a-hexahydro-2(1H)-isoquinolinecarboxylate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -63 ℃; for 0.5h;

With chloro-trimethyl-silane; In tetrahydrofuran; at -70 ℃; for 2h; Further stages;

DOI:10.1021/acs.jmedchem.5b01102

Reference yield:

tert-butyl 5-methyl-6-((triethylsilyl)oxy)-3,4,8,8a-tetrahydroisoquinoline-2(1H)-carboxylate → 1,1-dimethylethyl 6-hydroxy-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (1165923-89-6)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium formate / palladium diacetate / 2-methyltetrahydrofuran / 20 °C

2: tetrabutyl ammonium fluoride / ethyl acetate / 1.5 h

With tetrabutyl ammonium fluoride; potassium formate; palladium diacetate; In 2-methyltetrahydrofuran; ethyl acetate;

upstream raw materials:

di-tert-butyl dicarbonate

5-methyl-1,2,3,4-tetrahydroisoquinolin-6-ol

N-tert-butoxycarbonyl-4-(tetrahydropyrrole-1-yl)-1,2,3,6-tetrahydropyridine

N-tert-butyloxycarbonylpiperidin-4-one

Downstream raw materials:

1,1-dimethylethyl 5-methyl-6-{[(trifluoromethyl)sulfonyl]oxy}-3,4-dihydro-2(1H)-isoquinolinecarboxylate

5-methyl-1,2,3,4-tetrahydroisoquinolin-6-ol

5-(5-(2-(1,3-dihydroxypropan-2-yl)-5-methyl-1,2,3,4-tetrahydroisoquinolin-6-yl)-1,3,4-thiadiazol-2-yl)-2-isopropoxybenzonitrile hydrochloride

3-(6-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydroisoquinolin-2(1H)-yl)propanoic acid