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

Base Information

• Chemical Name: (3S,4S)-7-Benzyloxy-3-hydroxy-4-(4-methoxy-phenyl)-1,3,4,5-tetrahydro-benzo[b]azepin-2-one
• CAS No.: 138335-03-2
• Molecular Formula: C₂₄H₂₃NO₄
• Molecular Weight: 389.451
• Mol file: 138335-03-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about (3S,4S)-7-Benzyloxy-3-hydroxy-4-(4-methoxy-phenyl)-1,3,4,5-tetrahydro-benzo[b]azepin-2-one 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: 55.0%

(3R,4R)-7-Benzyloxy-3-hydroxy-4-(4-methoxy-phenyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-3-carboxylic acid methyl ester → (3S,4S)-7-Benzyloxy-3-hydroxy-4-(4-methoxy-phenyl)-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (138335-03-2) + (3R,4S)-7-Benzyloxy-3-hydroxy-4-(4-methoxy-phenyl)-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (138335-03-2)

Guidance literature:

With water; lithium iodide; In pyridine; Title compound not separated from byproducts; Heating;

DOI:10.1021/jm00082a018

Reference yield: 55.0%

(3R,4R)-7-Benzyloxy-3-hydroxy-4-(4-methoxy-phenyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-3-carboxylic acid methyl ester → (3S,4S)-7-Benzyloxy-3-hydroxy-4-(4-methoxy-phenyl)-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (138335-03-2) + (3R,4S)-7-Benzyloxy-3-hydroxy-4-(4-methoxy-phenyl)-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (138335-03-2)

Guidance literature:

With water; lithium iodide; In pyridine; Title compound not separated from byproducts; Heating;

DOI:10.1021/jm00082a018

Reference yield:

5-benzyloxy-2-nitrotoluene (22424-58-4) → (3S,4S)-7-Benzyloxy-3-hydroxy-4-(4-methoxy-phenyl)-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (138335-03-2)

Guidance literature:

Multi-step reaction with 5 steps

1: NaH / dimethylformamide / Ambient temperature

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

3: CH₃ONa / methanol / 3 h / Heating

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

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

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

DOI:10.1021/jm00082a020

upstream raw materials:

5-benzyloxy-2-nitrotoluene

dimethyl 2-(4-methoxybenzylidene)malonate

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

Downstream raw materials:

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