benzyl (2R,5S)-(+)-2-(2-iodoethyl)-5-(methoxymethoxymethyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: benzyl (2R,5S)-(+)-2-(2-iodoethyl)-5-(methoxymethoxymethyl)pyrrolidine-1-carboxylate
• CAS No.: 130753-19-4
• Molecular Formula: C₁₇H₂₄INO₄
• Molecular Weight: 433.286
• Mol file: 130753-19-4.mol

Synonyms:benzyl (2R,5S)-(+)-2-(2-iodoethyl)-5-(methoxymethoxymethyl)pyrrolidine-1-carboxylate

Chemical Property of benzyl (2R,5S)-(+)-2-(2-iodoethyl)-5-(methoxymethoxymethyl)pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2R,5S)-(+)-2-(2-iodoethyl)-5-(methoxymethoxymethyl)pyrrolidine-1-carboxylate

There total 7 articles about benzyl (2R,5S)-(+)-2-(2-iodoethyl)-5-(methoxymethoxymethyl)pyrrolidine-1-carboxylate 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: 99.0%

benzyl (2S,5R)-(-)-2-(methoxymethoxymethyl)-5-(2-p-tolylsulfonyloxyethyl)pyrrolidine-1-carboxylate (130753-18-3) → benzyl (2R,5S)-(+)-2-(2-iodoethyl)-5-(methoxymethoxymethyl)pyrrolidine-1-carboxylate (130753-19-4)

Guidance literature:

With sodium iodide; In acetone; for 5h; Ambient temperature;

Reference yield:

benzyl (2R,5S)-(-)-2-(2-hydroxyethyl)-5-(methoxymethoxymethyl)pyrrolidine-1-carboxylate (130753-17-2) → benzyl (2R,5S)-(+)-2-(2-iodoethyl)-5-(methoxymethoxymethyl)pyrrolidine-1-carboxylate (130753-19-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / pyridine / CH₂Cl₂ / 18 h / Ambient temperature

2: 99 percent / NaI / acetone / 5 h / Ambient temperature

With pyridine; sodium iodide; In dichloromethane; acetone;

Reference yield:

benzyl 3-oxo-8-azabicyclo[3,2,1]octane-8-carboxylate (130753-13-8) → benzyl (2R,5S)-(+)-2-(2-iodoethyl)-5-(methoxymethoxymethyl)pyrrolidine-1-carboxylate (130753-19-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 89 percent / n-BuLi, chiral pyrrolidine synthon / hexamethylphosphoric acid triamide / -100 °C

2: 1) O₃, 2) NaBH₄ / 1) CH₂Cl₂, MeOH, -78 deg C

4: (i-Pr)2NEt

5: super-hydride / tetrahydrofuran / 0 deg C to r.t.

6: pyridine

7: NaI / acetone

With pyridine; sodium tetrahydroborate; n-butyllithium; chiral pyrrolidine synthon; lithium triethylborohydride; ozone; N-ethyl-N,N-diisopropylamine; sodium iodide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; acetone;

DOI:10.1248/cpb.38.2072

upstream raw materials:

benzyl (2S,5R)-(-)-2-(methoxymethoxymethyl)-5-(2-p-tolylsulfonyloxyethyl)pyrrolidine-1-carboxylate

benzyl (2R,5S)-(-)-2-(2-hydroxyethyl)-5-(methoxymethoxymethyl)pyrrolidine-1-carboxylate

benzyl 3-oxo-8-azabicyclo[3,2,1]octane-8-carboxylate

methyl (2R,5S)-(-)-1-benzyloxycarbonyl-5-hydroxymethylpyrrolidin-2-ylethanoate

Downstream raw materials:

benzyl (2S,5S)-(-)-2-(methoxymethoxymethyl)-5-pent-4-enylpyrrolidine-1-carboxylate

benzyl (2S,5S)-2-but-1-enyl-5-pent-4-enylpyrrolidine-1-carboxylate

benzyl (2S,5S)-2-(but-1-enyl)-5-(4-oxopentyl)pyrrolidine-1-carboxylate