(2S,3S)-3-hydroxy-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,3S)-3-hydroxy-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester
• CAS No.: 160882-77-9
• Molecular Formula: C₂₅H₂₁NO₄
• Molecular Weight: 399.446
• Mol file: 160882-77-9.mol

Synonyms:(2S,3S)-3-hydroxy-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester

Chemical Property of (2S,3S)-3-hydroxy-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3-hydroxy-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester

There total 6 articles about (2S,3S)-3-hydroxy-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl 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: 80.0%

(2S)-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester (160882-76-8) → (2S,3S)-3-hydroxy-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester (160882-77-9)

Guidance literature:

With oxodiperoxymolybdenumpyridine hexamethylphosphoric triamide complex; sodium hexamethyldisilazane; In tetrahydrofuran; from -78 degC to -23 degC;

DOI:10.1016/S0040-4039(00)74441-8

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → (2S,3S)-3-hydroxy-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester (160882-77-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) chlorotrimethylsilane, Et₃N, 2.) Et₃N, Pb(NO₃)2 / 1) CH₂Cl₂, reflux, 1 h; 2) CH₂Cl₂, MeOH, rt, 96 h

2: 100 percent / DMSO, oxalyl chloride / CH₂Cl₂ / 0.5 h / -60 °C

3: 1.) NaHMDS, 2.) MoOPH / 1) THF, -78 deg C, 2 h; 2) THF, -78 - -15 deg C, 2.5 h

With chloro-trimethyl-silane; lead(II) nitrate; oxalyl dichloride; MoO₅*pyridine*HMPA; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; In dichloromethane;

DOI:10.1021/jo9604245

Reference yield:

(2S,4R)-4-hydroxy-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester (179990-59-1) → (2S,3S)-3-hydroxy-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester (160882-77-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / DMSO, oxalyl chloride / CH₂Cl₂ / 0.5 h / -60 °C

2: 1.) NaHMDS, 2.) MoOPH / 1) THF, -78 deg C, 2 h; 2) THF, -78 - -15 deg C, 2.5 h

With oxalyl dichloride; MoO₅*pyridine*HMPA; sodium hexamethyldisilazane; dimethyl sulfoxide; In dichloromethane;

DOI:10.1021/jo9604245

upstream raw materials:

(2S)-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester

9-bromo-9-phenyl-9H-fluorene

L-4-hydroxyproline methyl ester hydrochloride

(2S,4R)-4-hydroxy-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester

Downstream raw materials:

1,4-dideoxy-1,4-imino-D-mannitol hydrochloride

1-[(3aS,4S,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-ethanone

1-[(3aS,4S,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-2-fluoro-ethanone

(3aS,4S,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carboxylic acid methyl ester