2-[2-(5-Benzyloxy-2-nitro-phenyl)-1-(4-methoxy-phenyl)-ethyl]-malonic acid dimethyl ester

Base Information

• Chemical Name: 2-[2-(5-Benzyloxy-2-nitro-phenyl)-1-(4-methoxy-phenyl)-ethyl]-malonic acid dimethyl ester
• CAS No.: 138334-86-8
• Molecular Formula: C₂₇H₂₇NO₈
• Molecular Weight: 493.513
• Mol file: 138334-86-8.mol

Synonyms:2-[2-(5-Benzyloxy-2-nitro-phenyl)-1-(4-methoxy-phenyl)-ethyl]-malonic acid dimethyl ester

Chemical Property of 2-[2-(5-Benzyloxy-2-nitro-phenyl)-1-(4-methoxy-phenyl)-ethyl]-malonic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[2-(5-Benzyloxy-2-nitro-phenyl)-1-(4-methoxy-phenyl)-ethyl]-malonic acid dimethyl ester

There total 1 articles about 2-[2-(5-Benzyloxy-2-nitro-phenyl)-1-(4-methoxy-phenyl)-ethyl]-malonic acid dimethyl 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: 67.0%

5-benzyloxy-2-nitrotoluene (22424-58-4) + dimethyl 2-(4-methoxybenzylidene)malonate (7443-25-6) → 2-[2-(5-Benzyloxy-2-nitro-phenyl)-1-(4-methoxy-phenyl)-ethyl]-malonic acid dimethyl ester (138334-86-8)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1021/jm00082a018

Reference yield: 100.0%

2-[2-(5-Benzyloxy-2-nitro-phenyl)-1-(4-methoxy-phenyl)-ethyl]-malonic acid dimethyl ester (138334-86-8) → 2-[2-(2-Amino-5-benzyloxy-phenyl)-1-(4-methoxy-phenyl)-ethyl]-malonic acid dimethyl ester

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; 1.) RT, 30 min, 2.) 50-55 deg C, 1 h;

DOI:10.1021/jm00082a018

Reference yield:

2-[2-(5-Benzyloxy-2-nitro-phenyl)-1-(4-methoxy-phenyl)-ethyl]-malonic acid dimethyl ester (138334-86-8) → (3S,4R)-7-Benzyloxy-1-(2-dimethylamino-ethyl)-3-hydroxy-4-(4-methoxy-phenyl)-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

Guidance literature:

Multi-step reaction with 5 steps

1: SnCl₂*2H₂O, conc. HCl / methanol / 4.5 h

2: CH₃ONa / methanol / 3 h / Heating

3: 1.) potassium hexamethyldisilazide, 2.) trimethylphosphite, O₂ / 1.) THF, -78 deg C, 1 h, 2.) THF, 0 deg C, 30 min

4: LiI, H₂O / pyridine / 1.5 h / Heating

5: 1.) NaH / 1.) DMF, 1 h, 2.) DMF, toluene, 80 deg C, 3 h

With hydrogenchloride; water; oxygen; sodium methylate; potassium hexamethylsilazane; sodium hydride; tin(ll) chloride; lithium iodide; phosphorous acid trimethyl ester; In pyridine; methanol;

DOI:10.1021/jm00082a020

upstream raw materials:

5-benzyloxy-2-nitrotoluene

dimethyl 2-(4-methoxybenzylidene)malonate

Downstream raw materials:

(3S,4S)-7-Benzyloxy-3-hydroxy-4-(4-methoxy-phenyl)-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

(3R,4S)-7-Benzyloxy-3-hydroxy-4-(4-methoxy-phenyl)-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

Acetic acid (3S,4R)-7-benzyloxy-1-(2-dimethylamino-ethyl)-4-(4-methoxy-phenyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl ester