(1R,3S)-2-Benzyl-1-(2-methoxycarbonyl-ethyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester

Base Information

• Chemical Name: (1R,3S)-2-Benzyl-1-(2-methoxycarbonyl-ethyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
• CAS No.: 148022-32-6
• Molecular Formula: C₂₄H₂₆N₂O₄
• Molecular Weight: 406.481

Synonyms:(1R,3S)-2-Benzyl-1-(2-methoxycarbonyl-ethyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester

Chemical Property of (1R,3S)-2-Benzyl-1-(2-methoxycarbonyl-ethyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (1R,3S)-2-Benzyl-1-(2-methoxycarbonyl-ethyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester

There total 4 articles about (1R,3S)-2-Benzyl-1-(2-methoxycarbonyl-ethyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 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%

methyl 4,4-dimethoxybutanoate (4220-66-0) + methyl N-benzyl-L-tryptophanate (63229-68-5) → (1R,3S)-2-Benzyl-1-(2-methoxycarbonyl-ethyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester (148022-32-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 168h;

DOI:10.1016/S0040-4039(00)01061-3

Reference yield:

Nb-benzylidene-L-tryptophan methyl ester (19779-75-0,67628-15-3) → (1R,3S)-2-Benzyl-1-(2-methoxycarbonyl-ethyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester (148022-32-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium borohydride / methanol / -10 °C

2: 90 percent / TFA / CH₂Cl₂ / 168 h / 20 °C

With sodium tetrahydroborate; trifluoroacetic acid; In methanol; dichloromethane; 1: Reduction / 2: Cyclization;

DOI:10.1016/S0040-4039(00)01061-3

Reference yield:

benzaldehyde (100-52-7) → (1R,3S)-2-Benzyl-1-(2-methoxycarbonyl-ethyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester (148022-32-6)

Guidance literature:

Multi-step reaction with 3 steps

1: methanol / 2 h / 20 °C

2: sodium borohydride / methanol / -10 °C

3: 90 percent / TFA / CH₂Cl₂ / 168 h / 20 °C

With sodium tetrahydroborate; trifluoroacetic acid; In methanol; dichloromethane; 1: Condensation / 2: Reduction / 3: Cyclization;

DOI:10.1016/S0040-4039(00)01061-3

upstream raw materials:

methyl 4,4-dimethoxybutanoate

methyl N-benzyl-L-tryptophanate

N_b-benzylidene-L-tryptophan methyl ester

benzaldehyde

Downstream raw materials:

(6S,10S)-(-)-5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

(1R,3S)-2-Benzyl-1-(2-methoxycarbonyl-ethyl)-9-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester

methyl trans-2-benzyl-3-methoxycarbonyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate

trans-2-benzyl-3-carboxy-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionic acid

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