(3R,6S)-5-(2-Benzyloxy-3,4-dimethoxy-phenyl)-3,6-dimethyl-1,2,3,6-tetrahydro-pyridine-2-carboxylic acid

Base Information

• Chemical Name: (3R,6S)-5-(2-Benzyloxy-3,4-dimethoxy-phenyl)-3,6-dimethyl-1,2,3,6-tetrahydro-pyridine-2-carboxylic acid
• CAS No.: 79953-16-5
• Molecular Formula: C₂₃H₂₇NO₅
• Molecular Weight: 397.471
• Mol file: 79953-16-5.mol

Synonyms:(3R,6S)-5-(2-Benzyloxy-3,4-dimethoxy-phenyl)-3,6-dimethyl-1,2,3,6-tetrahydro-pyridine-2-carboxylic acid

Chemical Property of (3R,6S)-5-(2-Benzyloxy-3,4-dimethoxy-phenyl)-3,6-dimethyl-1,2,3,6-tetrahydro-pyridine-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,6S)-5-(2-Benzyloxy-3,4-dimethoxy-phenyl)-3,6-dimethyl-1,2,3,6-tetrahydro-pyridine-2-carboxylic acid

There total 6 articles about (3R,6S)-5-(2-Benzyloxy-3,4-dimethoxy-phenyl)-3,6-dimethyl-1,2,3,6-tetrahydro-pyridine-2-carboxylic acid 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:

3,4-dimethoxy-(phenylmethoxy)benzaldehyde (6527-13-5) → (3R,6S)-5-(2-Benzyloxy-3,4-dimethoxy-phenyl)-3,6-dimethyl-1,2,3,6-tetrahydro-pyridine-2-carboxylic acid (79953-16-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) sodium hydride / 1.) DMSO, THF, -10 deg C, 5 min, 2.) -10 deg C (10 min), room temperature, 1 h

2: 97 percent / tetrahydrofuran / 1.) -20 deg C, 30 min, 2.) 0 deg C, 45 min, 3.) room temperature, 1 h

3: 1.) CrO₃, pyridine, 2.) 5percent HCl / 1.) methylene chloride, room temperature, 35 min, 2.) THF, room temperature, 10 h

4: 1. ) n-butyllithium, 2.) potassium tert-butoxide / 1.) THF, -78 deg C (5 min), -22 deg C (10 min), 2.) tert-butyl alcohol, room temperature, 1 h

5: 2.) aq. Ba(OH)2x8H₂O / 1.) xylene, reflux, 3d, 2.) dioxane, reflux, 24 h

With pyridine; chromium(VI) oxide; hydrogenchloride; barium dihydroxide; n-butyllithium; potassium tert-butylate; sodium hydride; In tetrahydrofuran;

DOI:10.1021/ja00366a028

Reference yield:

β-ethenyl-3,4-dimethoxy-2-(phenylmethoxy)benzeneethanol (74614-85-0) → (3R,6S)-5-(2-Benzyloxy-3,4-dimethoxy-phenyl)-3,6-dimethyl-1,2,3,6-tetrahydro-pyridine-2-carboxylic acid (79953-16-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) CrO₃, pyridine, 2.) 5percent HCl / 1.) methylene chloride, room temperature, 35 min, 2.) THF, room temperature, 10 h

2: 1. ) n-butyllithium, 2.) potassium tert-butoxide / 1.) THF, -78 deg C (5 min), -22 deg C (10 min), 2.) tert-butyl alcohol, room temperature, 1 h

3: 2.) aq. Ba(OH)2x8H₂O / 1.) xylene, reflux, 3d, 2.) dioxane, reflux, 24 h

With pyridine; chromium(VI) oxide; hydrogenchloride; barium dihydroxide; n-butyllithium; potassium tert-butylate;

DOI:10.1021/ja00366a028

Reference yield:

<3,4-dimethoxy-2-(phenylmethoxy)phenyl>oxirane (74614-84-9) → (3R,6S)-5-(2-Benzyloxy-3,4-dimethoxy-phenyl)-3,6-dimethyl-1,2,3,6-tetrahydro-pyridine-2-carboxylic acid (79953-16-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / tetrahydrofuran / 1.) -20 deg C, 30 min, 2.) 0 deg C, 45 min, 3.) room temperature, 1 h

2: 1.) CrO₃, pyridine, 2.) 5percent HCl / 1.) methylene chloride, room temperature, 35 min, 2.) THF, room temperature, 10 h

3: 1. ) n-butyllithium, 2.) potassium tert-butoxide / 1.) THF, -78 deg C (5 min), -22 deg C (10 min), 2.) tert-butyl alcohol, room temperature, 1 h

4: 2.) aq. Ba(OH)2x8H₂O / 1.) xylene, reflux, 3d, 2.) dioxane, reflux, 24 h

With pyridine; chromium(VI) oxide; hydrogenchloride; barium dihydroxide; n-butyllithium; potassium tert-butylate; In tetrahydrofuran;

DOI:10.1021/ja00366a028

upstream raw materials:

1-(1-ethyliddine-2-butenyl)-3,4-dimethoxy-2-(phenylmethoxy)benzene

3-(p-chlorophenyl)-50methoxyhydrantoin

3,4-dimethoxysalicylaldehyde

3,4-dimethoxy-(phenylmethoxy)benzaldehyde