(5S,7R,8S)-2-phenyl-8-hydroxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline

Base Information

• Chemical Name: (5S,7R,8S)-2-phenyl-8-hydroxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline
• CAS No.: 1007589-02-7
• Molecular Formula: C₁₈H₁₉NO
• Molecular Weight: 265.355
• Mol file: 1007589-02-7.mol

Synonyms:(5S,7R,8S)-2-phenyl-8-hydroxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline

Chemical Property of (5S,7R,8S)-2-phenyl-8-hydroxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,7R,8S)-2-phenyl-8-hydroxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline

There total 7 articles about (5S,7R,8S)-2-phenyl-8-hydroxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline 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: 91.0%

(5S,7R)-6,6-dimethyl-2-phenyl-5,7-methanoquinolin-8(5H)-one → (5S,7R,8S)-2-phenyl-8-hydroxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline (1007589-02-7)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 20 - 22 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1016/j.tet.2011.05.075

Reference yield:

C18H19NO (1316251-07-6) → (5S,7R,8S)-2-phenyl-8-hydroxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline (1007589-02-7) + (5S,7R,8R)-2-phenyl-8-hydroxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline

Guidance literature:

C₁₈H₁₉NO; With acetic anhydride; at 110 ℃; for 2h; Inert atmosphere;

With hydrogenchloride; In water; for 1.5h; Reflux; Inert atmosphere;

With sodium hydroxide; In water; pH=12 - 13; optical yield given as %de; Cooling with ice; Inert atmosphere;

DOI:10.1016/j.tet.2011.05.075

Reference yield:

pyridine (110-86-1) → (5S,7R,8S)-2-phenyl-8-hydroxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline (1007589-02-7) + (5S,7R,8R)-2-phenyl-8-hydroxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline

Guidance literature:

Multi-step reaction with 4 steps

1.1: iodine

2.1: ammonium acetate

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: acetic anhydride / 2 h / 110 °C / Inert atmosphere

4.2: 1.5 h / Reflux; Inert atmosphere

4.3: pH 12 - 13 / Cooling with ice; Inert atmosphere

With ammonium acetate; iodine; acetic anhydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; 2.1: Krohnke reaction / 4.1: Boekelheide rearrangement;

DOI:10.1016/j.tet.2011.05.075

upstream raw materials:

pyridine

C₁₈H₁₉NO

N-(Phenacyl)pyridinium

(+)-α-pinene

Downstream raw materials:

(5S,7R,8S)-2-phenyl-8-methoxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline