methyl (3S)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Base Information

• Chemical Name: methyl (3S)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate
• CAS No.: 611239-26-0
• Molecular Formula: C₁₁H₁₃NO₄
• Molecular Weight: 223.229
• DSSTox Substance ID: DTXSID501154891
• Mol file: 611239-26-0.mol

Synonyms:methyl (3S)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate;611239-26-0;SCHEMBL540057;JVKJKADJNQEXEA-QMMMGPOBSA-N;DTXSID501154891;STL532336;AKOS032429507;Methyl (3S)-1,2,3,4-tetrahydro-6,7-dihydroxy-3-isoquinolinecarboxylate;(S)-6,7-dihydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester

Chemical Property of methyl (3S)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Chemical Property:

• PSA: 78.79000
• LogP: 0.61390
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 223.08445790
• Heavy Atom Count: 16
• Complexity: 271

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CC2=CC(=C(C=C2CN1)O)O
• Isomeric SMILES: COC(=O)[C@@H]1CC2=CC(=C(C=C2CN1)O)O

Technology Process of methyl (3S)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

There total 2 articles about methyl (3S)-6,7-dihydroxy-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: 99.0%

methanol (67-56-1) + (3S)-6,7-Dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (34312-81-7,792898-30-7) → (S)-methyl 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (611239-26-0)

Guidance literature:

With hydrogenchloride; for 6h; Heating;

DOI:10.1016/S0040-4039(03)01785-4

Reference yield:

levodopa (59-92-7,90638-38-3) → (S)-methyl 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (611239-26-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / H₂SO₄; water / 24 h

2: 99 percent / HCl / 6 h / Heating

With hydrogenchloride; sulfuric acid; water; 1: Pictet-Spengler cyclization;

DOI:10.1016/S0040-4039(03)01785-4

Reference yield:

(S)-methyl 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (611239-26-0) → (S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(3,4-dimethoxy-phenyl)-propionyl]-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester (538367-15-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Ac₂O / 4 h

1.2: 87 percent / water / methanol

2.1: 90 percent / K₂CO₃ / acetone / Heating

3.1: 85 percent / HCl / methanol / 4 h / Heating

4.1: 80 percent / bis(2-oxo-3-oxazolidinyl) phosphinic chloride; Et₃N / CH₂Cl₂ / 4 h

With hydrogenchloride; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; acetic anhydride; potassium carbonate; triethylamine; In methanol; dichloromethane; acetone;

DOI:10.1016/S0040-4039(03)01785-4

upstream raw materials:

methanol

(3S)-6,7-Dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

levodopa

Downstream raw materials:

3-(3,4-dimethoxy-benzyl)-8,9-dimethoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione

(3S,11aS)-3-(3,4-Dimethoxy-benzyl)-8,9-dimethoxy-1,4-dioxo-1,3,4,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinoline-2-carboxylic acid isopropyl ester

(3S,11aS)-3-(3,4-Dimethoxy-benzyl)-1-hydroxy-8,9-dimethoxy-4-oxo-1,3,4,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinoline-2-carboxylic acid isopropyl ester

(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(3,4-dimethoxy-phenyl)-propionyl]-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester