(2R,5S)-N-benzyloxycarbonyl-2-methoxycarbonyl-5-(2,2-dimethoxyethyl)-pyrrolidine

Base Information

• Chemical Name: (2R,5S)-N-benzyloxycarbonyl-2-methoxycarbonyl-5-(2,2-dimethoxyethyl)-pyrrolidine
• CAS No.: 936564-39-5
• Molecular Formula: C₁₈H₂₅NO₆
• Molecular Weight: 351.4
• Mol file: 936564-39-5.mol

Synonyms:(2R,5S)-N-benzyloxycarbonyl-2-methoxycarbonyl-5-(2,2-dimethoxyethyl)-pyrrolidine

Chemical Property of (2R,5S)-N-benzyloxycarbonyl-2-methoxycarbonyl-5-(2,2-dimethoxyethyl)-pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5S)-N-benzyloxycarbonyl-2-methoxycarbonyl-5-(2,2-dimethoxyethyl)-pyrrolidine

There total 5 articles about (2R,5S)-N-benzyloxycarbonyl-2-methoxycarbonyl-5-(2,2-dimethoxyethyl)-pyrrolidine 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: 92.0%

(2R,5S)-N-benzyloxycarbonyl-2-methoxycarbonyl-5-(2-oxoethyl)-pyrrolidine (936564-37-3) + trimethyl orthoformate (149-73-5) → (2R,5S)-N-benzyloxycarbonyl-2-methoxycarbonyl-5-(2,2-dimethoxyethyl)-pyrrolidine (936564-39-5)

Guidance literature:

With cerium(III) chloride; In methanol; for 0.5h;

DOI:10.1021/jo062532p

Reference yield:

(1R,5S)-N-benzyloxycarbonyl-2-oxo-8-azabicyclo[3.2.1]octane (936564-33-9) → (2R,5S)-N-benzyloxycarbonyl-2-methoxycarbonyl-5-(2,2-dimethoxyethyl)-pyrrolidine (936564-39-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 95 percent / p-toluenesulfonic acid monohydrate / 5 h / 80 °C

2.1: ozone / CH₂Cl₂ / -78 °C

2.2: 74 percent / triphenylphosphine / CH₂Cl₂

3.1: 92 percent / cerium(III) chloride heptahydrate / methanol / 0.5 h

With cerium(III) chloride; toluene-4-sulfonic acid; ozone; In methanol; dichloromethane;

DOI:10.1021/jo062532p

Reference yield:

(1R,5S)-N-benzyloxycarbonyl-2-methoxy-8-azabicyclo[3.2.1]oct-2-ene (936564-35-1) → (2R,5S)-N-benzyloxycarbonyl-2-methoxycarbonyl-5-(2,2-dimethoxyethyl)-pyrrolidine (936564-39-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ozone / CH₂Cl₂ / -78 °C

1.2: 74 percent / triphenylphosphine / CH₂Cl₂

2.1: 92 percent / cerium(III) chloride heptahydrate / methanol / 0.5 h

With cerium(III) chloride; ozone; In methanol; dichloromethane;

DOI:10.1021/jo062532p

upstream raw materials:

(2R,5S)-N-benzyloxycarbonyl-2-methoxycarbonyl-5-(2-oxoethyl)-pyrrolidine

trimethyl orthoformate

(1R,5S)-N-benzyloxycarbonyl-2-oxo-8-azabicyclo[3.2.1]octane

(1R,5S)-N-benzyloxycarbonyl-2-methoxy-8-azabicyclo[3.2.1]oct-2-ene