1,4-Methano-1H-3-benzazepine-3,4(2H,5H)-dicarboxylic acid, 8-methoxy-1-[(phenylthio)methyl]-, 3-(phenylmethyl) ester, (1S,4R)-

Base Information

• Chemical Name: 1,4-Methano-1H-3-benzazepine-3,4(2H,5H)-dicarboxylic acid, 8-methoxy-1-[(phenylthio)methyl]-, 3-(phenylmethyl) ester, (1S,4R)-
• CAS No.: 359882-20-5
• Molecular Formula: C28H27NO5S
• Molecular Weight: 489.592
• Mol file: 359882-20-5.mol

Synonyms:

Chemical Property of 1,4-Methano-1H-3-benzazepine-3,4(2H,5H)-dicarboxylic acid, 8-methoxy-1-[(phenylthio)methyl]-, 3-(phenylmethyl) ester, (1S,4R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,4-Methano-1H-3-benzazepine-3,4(2H,5H)-dicarboxylic acid, 8-methoxy-1-[(phenylthio)methyl]-, 3-(phenylmethyl) ester, (1S,4R)-

There total 7 articles about 1,4-Methano-1H-3-benzazepine-3,4(2H,5H)-dicarboxylic acid, 8-methoxy-1-[(phenylthio)methyl]-, 3-(phenylmethyl) ester, (1S,4R)- 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:

(1S,4R)-3-benzyloxycarbonyl-8-methoxy-4-methoxycarbonyl-1-phenylthiomethyl-2,3,4,5-tetrahydro-1,4-methano-3-benzazepine (359882-26-1) → (1S,9R)-4-Methoxy-1-phenylsulfanylmethyl-10-aza-tricyclo[7.2.1.02,7]dodeca-2(7),3,5-triene-9,10-dicarboxylic acid 10-benzyl ester (359882-20-5)

Guidance literature:

With sodium hydroxide; In methanol; for 2h; Heating;

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

Reference yield:

(R)-1-benzyloxycarbonyl-2-(2-bromo-4-methoxyphenyl)methyl-2-methoxycarbonyl-4-oxopyrrolidine (359882-24-9) → (1S,9R)-4-Methoxy-1-phenylsulfanylmethyl-10-aza-tricyclo[7.2.1.02,7]dodeca-2(7),3,5-triene-9,10-dicarboxylic acid 10-benzyl ester (359882-20-5)

Guidance literature:

Multi-step reaction with 3 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

With sodium hydroxide; n-butyllithium; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In tetrahydrofuran; methanol; hexane; benzene; 1.2: Horner reaction / 1.3: Horner reaction;

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

Reference yield:

(2R,4R)-1-benzyloxycarbonyl-2-[(2-bromo-4-methoxyphenyl)methyl]-4-hydroxy-2-(methoxycarbonyl)pyrrolidine (359882-23-8) → (1S,9R)-4-Methoxy-1-phenylsulfanylmethyl-10-aza-tricyclo[7.2.1.02,7]dodeca-2(7),3,5-triene-9,10-dicarboxylic acid 10-benzyl ester (359882-20-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 97 percent / PCC; Florisil / CH₂Cl₂ / 20 °C

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

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

2.3: 80 percent / NaH / tetrahydrofuran / 20 °C

3.1: 76 percent / Bu₃SnH; AIBN / benzene / 3.67 h / Heating

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

With sodium hydroxide; florisil; n-butyllithium; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; pyridinium chlorochromate; In tetrahydrofuran; methanol; hexane; dichloromethane; benzene; 2.2: Horner reaction / 2.3: Horner reaction;

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

upstream raw materials:

(1S,4R)-3-benzyloxycarbonyl-8-methoxy-4-methoxycarbonyl-1-phenylthiomethyl-2,3,4,5-tetrahydro-1,4-methano-3-benzazepine

diphenyl(phenylthiomethyl)phosphine oxide

(R)-1-benzyloxycarbonyl-2-(2-bromo-4-methoxyphenyl)methyl-2-methoxycarbonyl-4-oxopyrrolidine

(2R,4R)-1-benzyloxycarbonyl-2-[(2-bromo-4-methoxyphenyl)methyl]-4-hydroxy-2-(methoxycarbonyl)pyrrolidine

Downstream raw materials:

(-)-aphanorphine

(+)-8-O-methylaphanorphine

(1S,4R)-3-benzyloxycarbonyl-8-methoxy-1-phenylthiomethyl-2,3,4,5-tetrahydro-1,4-methano-3-benzazepine