1,2-Pyrrolidinedicarboxylic acid, 2-[(2-bromo-4-methoxyphenyl)methyl]-4-hydroxy-, 2-methyl 1-(phenylmethyl) ester, (2R,4R)-

Base Information

• Chemical Name: 1,2-Pyrrolidinedicarboxylic acid, 2-[(2-bromo-4-methoxyphenyl)methyl]-4-hydroxy-, 2-methyl 1-(phenylmethyl) ester, (2R,4R)-
• CAS No.: 359882-23-8
• Molecular Formula: C22H24BrNO6
• Molecular Weight: 478.34
• Mol file: 359882-23-8.mol

Synonyms:

Chemical Property of 1,2-Pyrrolidinedicarboxylic acid, 2-[(2-bromo-4-methoxyphenyl)methyl]-4-hydroxy-, 2-methyl 1-(phenylmethyl) ester, (2R,4R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-Pyrrolidinedicarboxylic acid, 2-[(2-bromo-4-methoxyphenyl)methyl]-4-hydroxy-, 2-methyl 1-(phenylmethyl) ester, (2R,4R)-

There total 1 articles about 1,2-Pyrrolidinedicarboxylic acid, 2-[(2-bromo-4-methoxyphenyl)methyl]-4-hydroxy-, 2-methyl 1-(phenylmethyl) ester, (2R,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: 68.0%

(4R)-1-benzyloxycarbonyl-2-[(2-bromo-4-methoxyphenyl)methyl]-4-(tert-butyldimethylsilyloxy)-2-(methoxycarbonyl)pyrrolidine → (2R,4R)-1-benzyloxycarbonyl-2-[(2-bromo-4-methoxyphenyl)methyl]-4-hydroxy-2-(methoxycarbonyl)pyrrolidine (359882-23-8) + (2S,4R)-1-benzyloxycarbonyl-2-[(2-bromo-4-methoxyphenyl)methyl]-4-hydroxy-2-(methoxycarbonyl)pyrrolidine

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

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

Reference yield: 97.0%

(2R,4R)-1-benzyloxycarbonyl-2-[(2-bromo-4-methoxyphenyl)methyl]-4-hydroxy-2-(methoxycarbonyl)pyrrolidine (359882-23-8) → (R)-1-benzyloxycarbonyl-2-(2-bromo-4-methoxyphenyl)methyl-2-methoxycarbonyl-4-oxopyrrolidine (359882-24-9)

Guidance literature:

With florisil; pyridinium chlorochromate; In dichloromethane; at 20 ℃;

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,4R)-3-benzyloxycarbonyl-8-methoxy-1-phenylthiomethyl-2,3,4,5-tetrahydro-1,4-methano-3-benzazepine (359882-21-6)

Guidance literature:

Multi-step reaction with 6 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

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

6.1: 530 mg / Bu₃SnH; AIBN / benzene / 3 h / Heating

With dmap; sodium hydroxide; florisil; n-butyllithium; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridinium chlorochromate; In tetrahydrofuran; methanol; hexane; dichloromethane; benzene; 2.2: Horner reaction / 2.3: Horner reaction / 6.1: Barton decarboxylation;

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

Downstream raw materials:

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

(-)-aphanorphine

(+)-8-O-methylaphanorphine

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