ethyl (3S,4aR,6S,8aR)-6-(2-cyanophenylamino)-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate

Base Information

• Chemical Name: ethyl (3S,4aR,6S,8aR)-6-(2-cyanophenylamino)-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate
• CAS No.: 503177-10-4
• Molecular Formula: C₂₁H₂₇N₃O₄
• Molecular Weight: 385.463
• Mol file: 503177-10-4.mol

Synonyms:ethyl (3S,4aR,6S,8aR)-6-(2-cyanophenylamino)-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate

Chemical Property of ethyl (3S,4aR,6S,8aR)-6-(2-cyanophenylamino)-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (3S,4aR,6S,8aR)-6-(2-cyanophenylamino)-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate

There total 1 articles about ethyl (3S,4aR,6S,8aR)-6-(2-cyanophenylamino)-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-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: 32.0%

ethyl (3S,4aR,8aR)-6-oxo-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate + anthranilic acid nitrile (1885-29-6) → ethyl (3S,4aR,6S,8aR)-6-(2-cyanophenylamino)-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate (503177-10-4)

Guidance literature:

With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; at 20 ℃; for 27h;

DOI:10.1021/jm0491952

Reference yield:

ethyl (3S,4aR,6S,8aR)-6-(2-cyanophenylamino)-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate (503177-10-4) → (3S,4aR,6S,8aR)-6-[2-(1H-Tetrazol-5-yl)-phenylamino]-octahydro-isoquinoline-2,3-dicarboxylic acid 3-ethyl ester 2-methyl ester (503177-11-5)

Guidance literature:

With azido tributyltin (IV); at 80 ℃; for 72h;

DOI:10.1021/jm0491952

Reference yield:

ethyl (3S,4aR,6S,8aR)-6-(2-cyanophenylamino)-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate (503177-10-4) → (3S,4aR,6S,8aR)-6-[2-(1H-Tetrazol-5-yl)-phenylamino]-decahydro-isoquinoline-3-carboxylic acid (503176-97-4)

Guidance literature:

Multi-step reaction with 2 steps

1: n-Bu₃SnN₃ / 72 h / 80 °C

2: 0.060 g / aq. HCl / 72 h / 90 °C

With hydrogenchloride; azido tributyltin (IV);

DOI:10.1021/jm0491952

upstream raw materials:

anthranilic acid nitrile

Downstream raw materials:

(3S,4aR,6S,8aR)-6-[2-(1H-Tetrazol-5-yl)-phenylamino]-octahydro-isoquinoline-2,3-dicarboxylic acid 3-ethyl ester 2-methyl ester

(3S,4aR,6S,8aR)-6-[2-(1H-Tetrazol-5-yl)-phenylamino]-decahydro-isoquinoline-3-carboxylic acid