(S)-Benzyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Base Information

• Chemical Name: (S)-Benzyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate
• CAS No.: 77497-96-2
• Molecular Formula: C17H17NO2^.HCl
• Molecular Weight: 267.327
• Hs Code.: 2933499090
• UNII: E784E3AR7M
• DSSTox Substance ID: DTXSID101179439
• Nikkaji Number: J239.653J
• Mol file: 77497-96-2.mol

Synonyms:77497-96-2;(S)-Benzyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate;E784E3AR7M;benzyl (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate;(3S)-1,2,3,4-Tetrahydro-isoquinoline-3-carboxylic acid benzyl ester;Benzyl (3S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate;Benzyl (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate Hydrochloride;3-Benzyloxycarbonyl-1,2,3,4-tetrahydro-isoquinoline (S)-;3-Isoquinolinecarboxylic acid, 1,2,3,4-tetrahydro-, phenylmethyl ester, (3S)-;UNII-E784E3AR7M;SCHEMBL7677497;DTXSID101179439;AKOS017344669;A9808;CS-0455631;(S)-Benzyl1,2,3,4-tetrahydroisoquinoline-3-carboxylate;Benzyl (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate;1,2,3,4-Tetrahydroisoquinoline-3alpha-carboxylic acid benzyl ester;Phenylmethyl (3S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate

Chemical Property of (S)-Benzyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Chemical Property:

• Vapor Pressure: 5.5E-07mmHg at 25°C
• Refractive Index: 1.584
• Boiling Point: 411.6 °C at 760 mmHg
• Flash Point: 202.8 °C
• PSA: 38.33000
• Density: 1.159g/cm3
• LogP: 2.77310
• Storage Temp.: Refrigerator
• Solubility.: Dimethyl Sulfoxide, Methanol
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 267.125928785
• Heavy Atom Count: 20
• Complexity: 325

Purity/Quality:

99%, ^*data from raw suppliers

Benzyl(3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylatehydrochloride 98 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(NCC2=CC=CC=C21)C(=O)OCC3=CC=CC=C3
• Isomeric SMILES: C1[C@H](NCC2=CC=CC=C21)C(=O)OCC3=CC=CC=C3

Technology Process of (S)-Benzyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate

There total 4 articles about (S)-Benzyl 1,2,3,4-tetrahydroisoquinoline-3-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:

benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinoline carboxylate p-toluenesulfonic acid salt (77497-97-3) → (S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, phenylmethylester (77497-96-2)

Guidance literature:

With sodium hydrogencarbonate; In ethyl acetate; Yield given;

DOI:10.1248/cpb.31.312

Reference yield:

L-Tic-OH (74163-81-8) + benzyl alcohol (100-51-6,185532-71-2) → (S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, phenylmethylester (77497-96-2)

Guidance literature:

With PPA; at 95 - 105 ℃; for 4h;

DOI:10.1021/jm00160a026

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → (S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, phenylmethylester (77497-96-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: L-phenylalanine; hydrogenchloride; formaldehyd / water / 4 h / 100 °C

1.2: 5 h

2.1: sodium hydrogencarbonate / water

With hydrogenchloride; formaldehyd; L-phenylalanine; sodium hydrogencarbonate; In water;

DOI:10.3987/COM-14-13029

upstream raw materials:

benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinoline carboxylate p-toluenesulfonic acid salt

L-Tic-OH

benzyl alcohol

Downstream raw materials:

(S)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide

(S)-N-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxamide

(S)-N-[(4-methylphenyl)sulfonyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide

(S)-N-[(1R)-1-phenylethyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide

Refernces

• 1、 -. "CRYSTALLINE FORM OF QUINAPRIL HYDROCHLORIDE AND PROCESS FOR PREPARING THE SAME". Page 24;13;16. . Retrieved 2008/06/13.
• 2、 Hayashi,Ozaki,Nunami,Yoneda. "Facile preparation of optically pure (3S)- and (3R)- 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid". . p. 312 - 314. Retrieved 2007/10/02.