1-Isoquinolineacetic acid,1,2,3,4-tetrahydro-,methyl ester,(R)- (9CI)

Base Information

• Chemical Name: 1-Isoquinolineacetic acid,1,2,3,4-tetrahydro-,methyl ester,(R)- (9CI)
• CAS No.: 156545-91-4
• Molecular Formula: C₁₂H₁₅NO₂
• Molecular Weight: 205.257
• Mol file: 156545-91-4.mol

Synonyms:1-Isoquinolineacetic acid,1,2,3,4-tetrahydro-,methyl ester,(R)- (9CI)

Chemical Property of 1-Isoquinolineacetic acid,1,2,3,4-tetrahydro-,methyl ester,(R)- (9CI)

Chemical Property:

• PSA: 38.33000
• LogP: 1.76530

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Isoquinolineacetic acid,1,2,3,4-tetrahydro-,methyl ester,(R)- (9CI)

There total 9 articles about 1-Isoquinolineacetic acid,1,2,3,4-tetrahydro-,methyl ester,(R)- (9CI) 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: 73.0%

(1R,1'R)-2-(2-hydroxy-1-phenylethyl)-1-methoxycarbonylmethyl-1,2,3,4-tetrahydroisoquinoline (156545-86-7) → (R)-1-methoxycarbonylmethyl-1,2,3,4-tetrahydroisoquinoline (156545-91-4)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; for 2h; Ambient temperature;

DOI:10.1248/cpb.42.796

Reference yield:

1-isopropoxycarbonylmethyl-1H-isoquinoline-2-carboxylic acid 2,2,2-trichloro-ethyl ester (872087-83-7) → (R)-1-methoxycarbonylmethyl-1,2,3,4-tetrahydroisoquinoline (156545-91-4)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylsilane; trifluoroacetic acid / CH₂Cl₂ / 0 - 23 °C

2: zinc; acetic acid / tetrahydrofuran; H₂O / 6 h / 23 °C

3: methanol / 23 °C

With triethylsilane; acetic acid; trifluoroacetic acid; zinc; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1002/anie.200502277

Reference yield:

1-isopropoxycarbonylmethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid 2,2,2-trichloro-ethyl ester (872087-95-1) → (R)-1-methoxycarbonylmethyl-1,2,3,4-tetrahydroisoquinoline (156545-91-4)

Guidance literature:

Multi-step reaction with 2 steps

1: zinc; acetic acid / tetrahydrofuran; H₂O / 6 h / 23 °C

2: methanol / 23 °C

With acetic acid; zinc; In tetrahydrofuran; methanol; water;

DOI:10.1002/anie.200502277

upstream raw materials:

(1R,1'R)-2-(2-hydroxy-1-phenylethyl)-1-methoxycarbonylmethyl-1,2,3,4-tetrahydroisoquinoline

(1,2,3,4-tetrahydro-isoquinolin-1-yl)-acetic acid isopropyl ester

sodium methylate

1-isopropoxycarbonylmethyl-1H-isoquinoline-2-carboxylic acid 2,2,2-trichloro-ethyl ester

Downstream raw materials:

(R)-2-(2-benzyloxycarbonylethyl)-1-methoxycarbonylmethyl-1,2,3,4-tetrahydroisoquinoline

Refernces

• 1、 Paal, Tihamer A.,Forro, Eniko,Fueloep, Ferenc,Liljeblad, Arto,Kanerva, Liisa T.. "Lipase-catalyzed kinetic resolution of 1,2,3,4-tetrahydroisoquinoline-1-acetic acid esters". experimental part. p. 2784 - 2788. Retrieved 2009/06/18.
• 2、 Takeuchi,Kamada,Nishimura,Nishioka,Nishikawa,Hashigaki,Yamamoto,Harayama. "Alkoxycarbonylmethylation of (3R,10bS)-3-phenyl-2,3,5,6-tetrahydro-10bH-oxazolo[2,3-a]isoquinoline". . p. 796 - 801. Retrieved 2007/10/02.