(2S,4R)-3,3-dimethyl-4-hydroxy-N-(9-phenylfluoren-9-yl)proline benzyl ester

Base Information

• Chemical Name: (2S,4R)-3,3-dimethyl-4-hydroxy-N-(9-phenylfluoren-9-yl)proline benzyl ester
• CAS No.: 173913-64-9
• Molecular Formula: C₃₃H₃₁NO₃
• Molecular Weight: 489.614
• Mol file: 173913-64-9.mol

Synonyms:(2S,4R)-3,3-dimethyl-4-hydroxy-N-(9-phenylfluoren-9-yl)proline benzyl ester

Chemical Property of (2S,4R)-3,3-dimethyl-4-hydroxy-N-(9-phenylfluoren-9-yl)proline benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S,4R)-3,3-dimethyl-4-hydroxy-N-(9-phenylfluoren-9-yl)proline benzyl ester

There total 1 articles about (2S,4R)-3,3-dimethyl-4-hydroxy-N-(9-phenylfluoren-9-yl)proline 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: 38.0%

(2S)-3,3-dimethyl-4-oxo-N-(9-phenylfluoren-9-yl)proline benzyl ester (173913-63-8) → (2S,4R)-3,3-dimethyl-4-hydroxy-N-(9-phenylfluoren-9-yl)proline benzyl ester (173913-64-9) + (2S,4S)-3,3-dimethyl-4-hydroxy-N-(9-phenylfluoren-9-yl)proline benzyl ester (173913-65-0)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 0 ℃; for 5.5h;

DOI:10.1021/jo9514984

Reference yield: 93.0%

di-tert-butyl dicarbonate (24424-99-5) + (2S,4R)-3,3-dimethyl-4-hydroxy-N-(9-phenylfluoren-9-yl)proline benzyl ester (173913-64-9) → (2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxy-3,3-dimethylpyrrolidine-2-carboxylic acid (173913-66-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; for 48h; under 3800 Torr;

DOI:10.1021/jo9514984

Reference yield:

(2S,4R)-3,3-dimethyl-4-hydroxy-N-(9-phenylfluoren-9-yl)proline benzyl ester (173913-64-9) → (2S)-3,3-dimethyl-N-(t-butoxycarbonyl)proline benzyl ester

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 1 h, 3.) 4 deg C, overnight

2: 91 percent / AIBN, Bu₃SnH / xylene / 1 h / Heating

3: H₂ / Pd/C / methanol / 25 h / 3800 Torr

With 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; sodium hydride; palladium on activated charcoal; In methanol; xylene;

DOI:10.1021/jo9514984

upstream raw materials:

(2S)-3,3-dimethyl-4-oxo-N-(9-phenylfluoren-9-yl)proline benzyl ester

Downstream raw materials:

(2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxy-3,3-dimethylpyrrolidine-2-carboxylic acid

(2S,4R)-3,3-Dimethyl-4-methylsulfanylthiocarboxyoxy-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidine-2-carboxylic acid benzyl ester

1-(tert-butoxycarbonyl)-3,3-dimethyl-D,L-proline

(2S)-3,3-dimethyl-N-(9-phenylfluoren-9-yl)proline benzyl ester