tert-butyl (2S,3R)-2-benzyl-3--5-oxo-1-pyrrolidinecarboxylate

Base Information

• Chemical Name: tert-butyl (2S,3R)-2-benzyl-3--5-oxo-1-pyrrolidinecarboxylate
• CAS No.: 229981-33-3
• Molecular Formula: C₂₂H₃₅NO₄Si
• Molecular Weight: 405.61
• Mol file: 229981-33-3.mol

Synonyms:tert-butyl (2S,3R)-2-benzyl-3--5-oxo-1-pyrrolidinecarboxylate

Chemical Property of tert-butyl (2S,3R)-2-benzyl-3--5-oxo-1-pyrrolidinecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2S,3R)-2-benzyl-3--5-oxo-1-pyrrolidinecarboxylate

There total 12 articles about tert-butyl (2S,3R)-2-benzyl-3--5-oxo-1-pyrrolidinecarboxylate 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: 75.0%

(3R,4S)-N-(tert-butoxycarbonyl)-4-amino-3-(tert-butyldimethylsilyloxy)-1-hydroxy-5-phenylpentane (229981-31-1) → tert-butyl (2S,3R)-2-benzyl-3--5-oxo-1-pyrrolidinecarboxylate (229981-33-3)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide; for 18h; Ambient temperature;

DOI:10.1021/jo990200x

Reference yield: 72.0%

tert-butyl (2S,3R)-3-(tert-butyldimethylsilyloxy)-1-phenylhex-5-en-2-ylcarbamate (1337862-68-6) → tert-butyl (2S,3R)-2-benzyl-3--5-oxo-1-pyrrolidinecarboxylate (229981-33-3)

Guidance literature:

With sodium periodate; ruthenium(III) trichloride hydrate; In tetrachloromethane; water; acetonitrile; at 20 ℃; for 16h;

DOI:10.1016/j.tet.2011.07.049

Reference yield:

(4S,5R)-5-ethenyl-4-phenylmethyloxazolidin-2-one (124915-64-6) → tert-butyl (2S,3R)-2-benzyl-3--5-oxo-1-pyrrolidinecarboxylate (229981-33-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / Et₃N, DMAP / tetrahydrofuran / 5.5 h / Ambient temperature

2: 76 percent / Cs₂CO₃ / methanol / 25 h / Ambient temperature

3: 90 percent / imidazole / dimethylformamide / 2 h

4: 1.) 9-BBN, 2.) NaOH, H₂O₂ / 1.) THF, hexane, room temperature, 20 h, 2.) EtOH, 50 deg C, 1 h

5: 75 percent / PDC / dimethylformamide / 18 h / Ambient temperature

With 1H-imidazole; dmap; sodium hydroxide; dipyridinium dichromate; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; caesium carbonate; triethylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo990200x

upstream raw materials:

(3R,4S)-N-(tert-butoxycarbonyl)-4-amino-3-(tert-butyldimethylsilyloxy)-1-hydroxy-5-phenylpentane

(4S,5R)-5-ethenyl-4-phenylmethyloxazolidin-2-one

((1S,2R)-1-benzyl-2-hydroxybut-3-enyl)carbamic acid tert-butyl ester

(4S,5R)-N-(tert-butyloxycarbonyl)-5-ethenyl-4-phenylmethyl oxazolidin-2-one

Downstream raw materials:

(4S,5S)-5-Benzyl-1-(tert-butyloxycarbonyl)-4-hydroxypyrrolidin-2-one

(4R,5S)-5-Benzyl-4-hydroxy-2-oxopyrrolidine

(4S,5S)-5-Benzyl-2-oxo-4-hydroxypyrrolidine

(5S)-5-benzyl-4-hydroxy-1-t-butoxycarbonylpyrrol-2(5H)-one