(2R,2'S,4'S)-1-tert-butoxycarbonyl-2-(2-phenyl-1,3-dioxan-4-yl)pyrrolidin-3-one

Base Information

• Chemical Name: (2R,2'S,4'S)-1-tert-butoxycarbonyl-2-(2-phenyl-1,3-dioxan-4-yl)pyrrolidin-3-one
• CAS No.: 548458-36-2
• Molecular Formula: C₁₉H₂₅NO₅
• Molecular Weight: 347.411
• Mol file: 548458-36-2.mol

Synonyms:(2R,2'S,4'S)-1-tert-butoxycarbonyl-2-(2-phenyl-1,3-dioxan-4-yl)pyrrolidin-3-one

Chemical Property of (2R,2'S,4'S)-1-tert-butoxycarbonyl-2-(2-phenyl-1,3-dioxan-4-yl)pyrrolidin-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,2'S,4'S)-1-tert-butoxycarbonyl-2-(2-phenyl-1,3-dioxan-4-yl)pyrrolidin-3-one

There total 5 articles about (2R,2'S,4'S)-1-tert-butoxycarbonyl-2-(2-phenyl-1,3-dioxan-4-yl)pyrrolidin-3-one 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: 50.0%

di-tert-butyl dicarbonate (24424-99-5) + (2R,2'S,4'S)-1-benzyl-3-benzyloxy-2-(2-phenyl-1,3-dioxan-4-yl)-2,5-dihydro-1H-pyrrole (548458-33-9) → (2R,2'S,4'S)-1-tert-butoxycarbonyl-2-(2-phenyl-1,3-dioxan-4-yl)pyrrolidin-3-one (548458-36-2) + (2S,3R,2'S,4'S)-3-benzyloxy-1-tert-butoxycarbonyl-2-(2-phenyl-1,3-dioxan-4-yl)pyrrolidine

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 20h;

DOI:10.1002/chem.200390160

Reference yield: 37.0%

di-tert-butyl dicarbonate (24424-99-5) + (2R,2'S,4'S)-1-benzyl-3-benzyloxy-2-(2-phenyl-1,3-dioxan-4-yl)-2,5-dihydro-1H-pyrrole (548458-33-9) → (2R,2'S,4'S)-1-tert-butoxycarbonyl-2-(2-phenyl-1,3-dioxan-4-yl)pyrrolidin-3-one (548458-36-2) + (2R,2'S,4'S)-3-benzyloxy-1-tert-butoxycarbonyl-2-(2-phenyl-1,3-dioxan-4-yl)-2,5-dihydro-1H-pyrrole

Guidance literature:

With hydrogen; palladium dihydroxide; In ethanol; at 20 ℃; for 48h;

DOI:10.1002/chem.200390160

Reference yield:

[(2S,4S)-2-phenyl-1,3-dioxan-4-yl]methanol (103773-79-1) → (2R,2'S,4'S)-1-tert-butoxycarbonyl-2-(2-phenyl-1,3-dioxan-4-yl)pyrrolidin-3-one (548458-36-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -60 - 20 °C

2.1: 88 percent / MgSO₄ / CH₂Cl₂ / 3 h / 20 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -50 - -40 °C

3.2: 2.15 g / tetrahydrofuran; hexane / 16 h / -50 - 20 °C

4.1: 13 percent / H₂ / Pd(OH)2/C / ethanol / 48 h / 20 °C

With n-butyllithium; oxalyl dichloride; hydrogen; magnesium sulfate; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In tetrahydrofuran; ethanol; hexane; dichloromethane;

DOI:10.1002/chem.200390160

upstream raw materials:

di-tert-butyl dicarbonate

(2R,2'S,4'S)-1-benzyl-3-benzyloxy-2-(2-phenyl-1,3-dioxan-4-yl)-2,5-dihydro-1H-pyrrole

[(2S,4S)-2-phenyl-1,3-dioxan-4-yl]methanol

(2S,4S)-2-phenyl-1,3-dioxane-4-carboxaldehyde

Downstream raw materials:

(2S,3R,2'S,4'S)-1-tert-butoxycarbonyl-3-hydroxy-2-(2-phenyl-1,3-dioxan-4-yl)pyrrolidine