(3R,4aS,8aS)-3-((S)-2-tert-Butoxycarbonyl-pyrrolidine-1-carbonyl)-octahydro-isoquinoline-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (3R,4aS,8aS)-3-((S)-2-tert-Butoxycarbonyl-pyrrolidine-1-carbonyl)-octahydro-isoquinoline-2-carboxylic acid benzyl ester
• CAS No.: 173325-15-0
• Molecular Formula: C₂₇H₃₈N₂O₅
• Molecular Weight: 470.609
• Mol file: 173325-15-0.mol

Synonyms:(3R,4aS,8aS)-3-((S)-2-tert-Butoxycarbonyl-pyrrolidine-1-carbonyl)-octahydro-isoquinoline-2-carboxylic acid benzyl ester

Chemical Property of (3R,4aS,8aS)-3-((S)-2-tert-Butoxycarbonyl-pyrrolidine-1-carbonyl)-octahydro-isoquinoline-2-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4aS,8aS)-3-((S)-2-tert-Butoxycarbonyl-pyrrolidine-1-carbonyl)-octahydro-isoquinoline-2-carboxylic acid benzyl ester

There total 4 articles about (3R,4aS,8aS)-3-((S)-2-tert-Butoxycarbonyl-pyrrolidine-1-carbonyl)-octahydro-isoquinoline-2-carboxylic acid benzyl ester 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: 94.0%

proline tert-butyl ester (2812-46-6) + (3R,4aS,8aS)-Octahydro-isoquinoline-2,3-dicarboxylic acid 2-benzyl ester (169390-43-6,136465-85-5) → (3R,4aS,8aS)-3-((S)-2-tert-Butoxycarbonyl-pyrrolidine-1-carbonyl)-octahydro-isoquinoline-2-carboxylic acid benzyl ester (173325-15-0)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; 1.) 0 deg C, 3 h, 2.) RT, 24 h;

DOI:10.1021/jm00022a009

Reference yield:

(3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (103733-65-9) → (3R,4aS,8aS)-3-((S)-2-tert-Butoxycarbonyl-pyrrolidine-1-carbonyl)-octahydro-isoquinoline-2-carboxylic acid benzyl ester (173325-15-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / H₂, aq.HCl / 5percent Rh/Al₂O₃ / 16 h / 120 °C / 103430 Torr

2: 85 percent / aq.NaOH / tetrahydrofuran / 2 h / Ambient temperature; pH 9.8

3: 94 percent / HOBt, DCC / dimethylformamide / 1.) 0 deg C, 3 h, 2.) RT, 24 h

With hydrogenchloride; sodium hydroxide; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; Rh/Al₂O₃; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jm00022a009

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (3R,4aS,8aS)-3-((S)-2-tert-Butoxycarbonyl-pyrrolidine-1-carbonyl)-octahydro-isoquinoline-2-carboxylic acid benzyl ester (173325-15-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / aq.NaOH / tetrahydrofuran / 2 h / Ambient temperature; pH 9.8

2: 94 percent / HOBt, DCC / dimethylformamide / 1.) 0 deg C, 3 h, 2.) RT, 24 h

With sodium hydroxide; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jm00022a009

upstream raw materials:

proline tert-butyl ester

(3R,4aS,8aS)-Octahydro-isoquinoline-2,3-dicarboxylic acid 2-benzyl ester

benzyl chloroformate

(3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Downstream raw materials:

Cbz-R-cis-(4aS,8aS)-3-Piq-Pro-OH