Tert-butyl 3,4-dihydroisoquinoline-2(1H)-carboxylate

Base Information

• Chemical Name: Tert-butyl 3,4-dihydroisoquinoline-2(1H)-carboxylate
• CAS No.: 138350-92-2
• Molecular Formula: C14H19NO2
• Molecular Weight: 233.31
• European Community (EC) Number: 871-261-3
• DSSTox Substance ID: DTXSID90568407
• Nikkaji Number: J432.283E
• Wikidata: Q82454651
• Mol file: 138350-92-2.mol

Synonyms:138350-92-2;2(1H)-Isoquinolinecarboxylic acid, 3,4-dihydro-, 1,1-dimethylethyl ester;TERT-BUTYL 3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE;tert-butyl 1,2,3,4-tetrahydroisoquinoline-2-carboxylate;TERT-BUTYL 3,4-DIHYDRO-1H-ISOQUINOLINE-2-CARBOXYLATE;SCHEMBL1202402;DTXSID90568407;HTDOHIVUPFBSNR-UHFFFAOYSA-N;1,2,3,4-tetrahydro-isoquinoline-2-carboxylic acid tert-butyl ester;AKOS013102138;D86982;EN300-182165;N-(t-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline;tert-butyl 3,4-dihydro-2(1H)-isoquinolinecarboxylate;3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester;2(1H)-Isoquinolinecarboxylicacid,3,4-dihydro-,1,1-dimethylethylester

Chemical Property of Tert-butyl 3,4-dihydroisoquinoline-2(1H)-carboxylate

Chemical Property:

• Boiling Point: 334.2±31.0 °C(Predicted)
• PKA: -1.40±0.20(Predicted)
• PSA: 29.54000
• Density: 1.087±0.06 g/cm3(Predicted)
• LogP: 2.91770
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 233.141578849
• Heavy Atom Count: 17
• Complexity: 282

Purity/Quality:

tert-butyl1,2,3,4-tetrahydroisoquinoline-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC2=CC=CC=C2C1

Technology Process of Tert-butyl 3,4-dihydroisoquinoline-2(1H)-carboxylate

There total 12 articles about Tert-butyl 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: 100.0%

1,2,3,4-tetrahydroisoquinoline (91-21-4) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 1,2,3,4-tetrahydroisoquinoline-2-carboxylate (138350-92-2)

Guidance literature:

In dichloromethane; for 1h; Ambient temperature;

DOI:10.1002/jhet.5570280720

Reference yield: 95.0%

2-(tert-butoxycarbonyl)-1,2-dihydroisoquinoline (138350-89-7) → tert-butyl 1,2,3,4-tetrahydroisoquinoline-2-carboxylate (138350-92-2)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethyl acetate; for 12h; under 2585.7 Torr;

DOI:10.1139/v94-005

Reference yield: 53.0%

potassium (2-(tert-butoxycarbonylamino)ethyl) trifluoroborate salt + ortho-bromobenzaldehyde (6630-33-7) → tert-butyl 1,2,3,4-tetrahydroisoquinoline-2-carboxylate (138350-92-2)

Guidance literature:

potassium (2-(tert-butoxycarbonylamino)ethyl) trifluoroborate salt; ortho-bromobenzaldehyde; With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In water; toluene; at 80 ℃; for 16h; Sealed tube; Inert atmosphere;

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.joc.1c02302

upstream raw materials:

1,2,3,4-tetrahydroisoquinoline

di-tert-butyl dicarbonate

2-(tert-butoxycarbonyl)-1,2-dihydroisoquinoline

ortho-methylbenzylamine

Downstream raw materials:

N-benzoyl-1,2,3,4-tetrahydroisoquinoline

1-benzyl-1,2,3,4-tetrahydroisoquinoline

1,2,3,4-tetrahydroisoquinoline

2-methyl-1,2,3,4-tetrahydroisoquinoline