(1R,3S)-2-benzyl-3-methoxycarbonyl-1-methylcarboxy-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b> indole

Base Information

• Chemical Name: (1R,3S)-2-benzyl-3-methoxycarbonyl-1-methylcarboxy-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b> indole
• CAS No.: 101533-85-1
• Molecular Formula: C₂₃H₂₄N₂O₄
• Molecular Weight: 392.455
• Mol file: 101533-85-1.mol

Synonyms:(1R,3S)-2-benzyl-3-methoxycarbonyl-1-methylcarboxy-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b> indole

Chemical Property of (1R,3S)-2-benzyl-3-methoxycarbonyl-1-methylcarboxy-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b> indole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3S)-2-benzyl-3-methoxycarbonyl-1-methylcarboxy-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b> indole

There total 6 articles about (1R,3S)-2-benzyl-3-methoxycarbonyl-1-methylcarboxy-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b> indole 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: 90.0%

(E)-3-{Benzyl-[(S)-2-(1H-indol-3-yl)-1-methoxycarbonyl-ethyl]-amino}-acrylic acid methyl ester → (1R,3S)-2-benzyl-3-methoxycarbonyl-1-methylcarboxy-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b> indole (101533-85-1)

Guidance literature:

With trifluoroacetic acid; In chloroform; at -40 - 20 ℃; for 8h;

DOI:10.1021/acs.joc.6b02648

Reference yield:

(E)-3-{Benzyl-[(S)-2-(1H-indol-3-yl)-1-methoxycarbonyl-ethyl]-amino}-acrylic acid methyl ester → (1R,3S)-2-benzyl-3-methoxycarbonyl-1-methylcarboxy-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b> indole (101533-85-1) + (1S,3S)-2-benzyl-3-methoxycarbonyl-1-methoxycarbonylmethyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole (101533-78-2)

Guidance literature:

With trifluoroacetic acid; In chloroform; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1039/c39850001507

Reference yield:

methyl N-benzyl-L-tryptophanate (63229-68-5) → (1R,3S)-2-benzyl-3-methoxycarbonyl-1-methylcarboxy-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b> indole (101533-85-1)

Guidance literature:

Multi-step reaction with 2 steps

1: CHCl₃ / 120 h / Ambient temperature

2: trifluoroacetic acid / CHCl₃ / Ambient temperature

With trifluoroacetic acid; In chloroform;

DOI:10.1039/c39850001507

upstream raw materials:

benzyl bromide

(1R,3S)-3-methoxycarbonyl-1-methoxycarbonylmethyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole

methyl N-benzyl-L-tryptophanate

propynoic acid methyl ester

Downstream raw materials:

(1R,3S)-2-benzyl-3-methoxycarbonyl-1-methoxycarbonylmethyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole