(1S,3S)-methyl 2-benzyl-1-methyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

Base Information

• Chemical Name: (1S,3S)-methyl 2-benzyl-1-methyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate
• CAS No.: 91185-15-8
• Molecular Formula: C₂₁H₂₂N₂O₂
• Molecular Weight: 334.418
• Mol file: 91185-15-8.mol

Synonyms:(1S,3S)-methyl 2-benzyl-1-methyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

Chemical Property of (1S,3S)-methyl 2-benzyl-1-methyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of (1S,3S)-methyl 2-benzyl-1-methyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

There total 2 articles about (1S,3S)-methyl 2-benzyl-1-methyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-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: 90.0%

benzyl bromide (100-39-0) + (1S,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester (93598-06-2) → (1S,3S)-methyl 2-benzyl-1-methyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate (91185-15-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 81 ℃; for 5h;

DOI:10.1016/j.tetasy.2013.06.006

Reference yield:

Nb-Benzyl tryptophan methyl ester (63229-68-5,73327-10-3,84094-71-3) + acetaldehyde (75-07-0,9002-91-9) → (1S,3S)-methyl 2-benzyl-1-methyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate (91185-15-8) + methyl (1R,3S)-2-benzyl-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate (91166-30-2)

Guidance literature:

In benzene; at 78 ℃; Product distribution; other aldehydes or analoguous reaction of the corresponding isopropyl ester: diastereoselectivity; or multistep synthesis with 2) TFA;

DOI:10.1016/0040-4039(91)80847-Y

Reference yield: 95.0%

(1S,3S)-methyl 2-benzyl-1-methyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate (91185-15-8) → methyl 1'-benzyl-2'-methyl-2-oxospiro[indoline-3,3'-pyrrolidine]-5'-carboxylate

Guidance literature:

With trichloroisocyanuric acid; In tetrahydrofuran; water; at 20 ℃; for 0.5h; diastereoselective reaction;

DOI:10.1039/d1ra02381k

upstream raw materials:

N_b-Benzyl tryptophan methyl ester

acetaldehyde

benzyl bromide

(1S,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester