(1R)-1,3-dimethyl-2,3,4,5-tetrahydro-1H-1,4-methano-3-benzazepin-8-ol

Base Information

• Chemical Name: (1R)-1,3-dimethyl-2,3,4,5-tetrahydro-1H-1,4-methano-3-benzazepin-8-ol
• CAS No.: 118964-06-0
• Molecular Formula: C₁₃H₁₇NO
• Molecular Weight: 203.284
• Mol file: 118964-06-0.mol

Synonyms:1,4-Methano-1H-3-benzazepin-8-ol,2,3,4,5-tetrahydro-1,3-dimethyl-, (1R)- (9CI); (-)-8-Hydroxy-1,3-dimethyl-2,3,4,5-tetrahydro-1,4-methano-3-benzazepine;(-)-Aphanorphine; Aphanorphine

Chemical Property of (1R)-1,3-dimethyl-2,3,4,5-tetrahydro-1H-1,4-methano-3-benzazepin-8-ol

Chemical Property:

• Vapor Pressure: 0.000121mmHg at 25°C
• Boiling Point: 325.4°Cat760mmHg
• Flash Point: 159.1°C
• Density: 1.148g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R)-1,3-dimethyl-2,3,4,5-tetrahydro-1H-1,4-methano-3-benzazepin-8-ol

There total 50 articles about (1R)-1,3-dimethyl-2,3,4,5-tetrahydro-1H-1,4-methano-3-benzazepin-8-ol 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: 88.0%

(+)-8-O-methylaphanorphine (128524-63-0,791780-36-4) → (-)-aphanorphine (118964-06-0)

Guidance literature:

With boron tribromide; In dichloromethane; at -20 - 0 ℃; for 4h;

DOI:10.1055/s-2006-958931

Reference yield: 76.0%

ethyl (4R)-8-hydroxy-1-methyl-1,2,4,5-tetrahydro-3H-1,4-methanobenzo[d]azepine-3-carboxylate → (-)-aphanorphine (118964-06-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 60 ℃; for 18h; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.1c05274

Reference yield:

(R)-1-benzyloxycarbonyl-2-(2-bromo-4-methoxyphenyl)methyl-2-methoxycarbonyl-4-oxopyrrolidine (359882-24-9) → (-)-aphanorphine (118964-06-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: BuLi / hexane; tetrahydrofuran / -78 °C

1.2: CeCl₃ / tetrahydrofuran; hexane / -78 - 20 °C

1.3: 80 percent / NaH / tetrahydrofuran / 20 °C

2.1: 76 percent / Bu₃SnH; AIBN / benzene / 3.67 h / Heating

3.1: aq. NaOH / methanol / 2 h / Heating

4.1: DMAP; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride / benzene / 0.5 h / 20 °C

5.1: 530 mg / Bu₃SnH; AIBN / benzene / 3 h / Heating

6.1: 65 percent / W-2 Raney nickel / 6 h / Heating

7.1: BBr₃

With dmap; sodium hydroxide; n-butyllithium; 2,2'-azobis(isobutyronitrile); W-2 Raney nickel; tri-n-butyl-tin hydride; boron tribromide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; hexane; benzene; 1.2: Horner reaction / 1.3: Horner reaction / 5.1: Barton decarboxylation;

DOI:10.1016/S0957-4166(03)00530-5

upstream raw materials:

(+)-8-O-methylaphanorphine

1-methyl-2-(trimethylsilyl)ethyl (1S,3R)-3-[tert-buthoxycarbonyl(methyl)amino]-7-methoxy-2-oxo-1,2,3,4-tetrahydronaphthalene-1-carboxylate

C₁₄H₁₅NO₃

C₁₆H₂₁NO₂S₂

Refernces

• 1、 Medjahdi, Mohamed,Gonzalez-Gomez, Jose C.,Foubelo, Francisco,Yus, Miguel. "Concise route to (-)- and (+)-aphanorphine". experimental part. p. 2230 - 2234. Retrieved 2011/06/22.
• 2、 Tamura, Osamu,Yanagimachi, Takehiko,Ishibashi, Hiroyuki. "Synthesis of (-)-aphanorphine using a sulfur-directed aryl radical cyclization". . p. 3033 - 3041. Retrieved 2007/10/03.