methyl (3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylate

Base Information

• Chemical Name: methyl (3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylate
• CAS No.: 352015-84-0
• Molecular Formula: C₂₈H₂₈N₂O₅
• Molecular Weight: 472.541

Synonyms:methyl (3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylate

Chemical Property of methyl (3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylate

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Technology Process of methyl (3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylate

There total 2 articles about methyl (3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-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:

4-(benzyloxy)-3,5-dimethoxybenzaldehyde (6527-32-8) + L-tryptophan methyl ester (4299-70-1) → methyl (3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylate (352015-84-0)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 20h; Heating;

DOI:10.1016/S0960-894X(01)00136-6

Reference yield:

4-(benzyloxy)-3,5-dimethoxybenzaldehyde (6527-32-8) + L-tryptophan methyl ester (4299-70-1) → methyl (3S,1S)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylate (1046143-13-8) + methyl (3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylate (352015-84-0)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 18h; optical yield given as %de; Reflux; Inert atmosphere;

DOI:10.1016/j.bmcl.2008.05.022

Reference yield: 75.0%

methyl (3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylate (352015-84-0) → (3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (352015-85-1)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; Reflux; Inert atmosphere;

DOI:10.1016/j.bmcl.2008.05.022

upstream raw materials:

4-(benzyloxy)-3,5-dimethoxybenzaldehyde

L-tryptophan methyl ester

Downstream raw materials:

(3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid

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