(4S,5R)-4-hydroxy-5-methoxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine

Base Information

• Chemical Name: (4S,5R)-4-hydroxy-5-methoxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine
• CAS No.: 294196-28-4
• Molecular Formula: C₁₈H₂₁NO₄S
• Molecular Weight: 347.435
• Mol file: 294196-28-4.mol

Synonyms:(4S,5R)-4-hydroxy-5-methoxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine

Chemical Property of (4S,5R)-4-hydroxy-5-methoxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-4-hydroxy-5-methoxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine

There total 4 articles about (4S,5R)-4-hydroxy-5-methoxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine 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: 78.0%

(4S,5R)-4,5-dihydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (193686-94-1) + methyl iodide (74-88-4) → (4S,5R)-4-hydroxy-5-methoxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (294196-28-4)

Guidance literature:

(4S,5R)-4,5-dihydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine; With di(n-butyl)tin oxide; In tetrahydrofuran; toluene; for 5h; Heating;

methyl iodide; With tetrabutylammomium bromide; In tetrahydrofuran; toluene; for 2h; Heating;

DOI:10.1016/S0040-4020(00)00388-4

Reference yield:

5-hydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (19673-33-7) → (4S,5R)-4-hydroxy-5-methoxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (294196-28-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 93 percent / p-toluenesulfonic acid / toluene / 6 h / Heating

2.1: 69 percent / osmium tetroxide; 4-methylmorpholine N-oxide / acetone; 2-methyl-propan-2-ol; H₂O / 20 °C

3.1: lipase QL / 6 h / 20 °C

4.1: dibutyltin oxide / toluene; tetrahydrofuran / 5 h / Heating

4.2: 78 percent / tetrabutylammonium bromide / toluene; tetrahydrofuran / 2 h / Heating

With osmium(VIII) oxide; Lipase QL; di(n-butyl)tin oxide; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; acetone; toluene; tert-butyl alcohol; 1.1: Dehydration / 2.1: Oxidation / 3.1: Acetylation / 4.1: Cyclization / 4.2: Ring cleavage;

DOI:10.1016/S0040-4020(00)00388-4

Reference yield:

1-(p-toluenesulfonyl)-2,3-dihydro-1H-1-benzazepine (19673-34-8) → (4S,5R)-4-hydroxy-5-methoxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (294196-28-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 69 percent / osmium tetroxide; 4-methylmorpholine N-oxide / acetone; 2-methyl-propan-2-ol; H₂O / 20 °C

2.1: lipase QL / 6 h / 20 °C

3.1: dibutyltin oxide / toluene; tetrahydrofuran / 5 h / Heating

3.2: 78 percent / tetrabutylammonium bromide / toluene; tetrahydrofuran / 2 h / Heating

With osmium(VIII) oxide; Lipase QL; di(n-butyl)tin oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; acetone; toluene; tert-butyl alcohol; 1.1: Oxidation / 2.1: Acetylation / 3.1: Cyclization / 3.2: Ring cleavage;

DOI:10.1016/S0040-4020(00)00388-4

upstream raw materials:

(4S,5R)-4,5-dihydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine

methyl iodide

5-hydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine

1-(p-toluenesulfonyl)-2,3-dihydro-1H-1-benzazepine