(2S,4R)-methyl 1-benzyl-4-((triisopropylsilyl)oxy)pyrrolidine-2-carboxylate

Base Information

• Chemical Name: (2S,4R)-methyl 1-benzyl-4-((triisopropylsilyl)oxy)pyrrolidine-2-carboxylate
• CAS No.: 882990-54-7
• Molecular Formula: C₂₂H₃₇NO₃Si
• Molecular Weight: 391.626
• Mol file: 882990-54-7.mol

Synonyms:(2S,4R)-methyl 1-benzyl-4-((triisopropylsilyl)oxy)pyrrolidine-2-carboxylate

Chemical Property of (2S,4R)-methyl 1-benzyl-4-((triisopropylsilyl)oxy)pyrrolidine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of (2S,4R)-methyl 1-benzyl-4-((triisopropylsilyl)oxy)pyrrolidine-2-carboxylate

There total 4 articles about (2S,4R)-methyl 1-benzyl-4-((triisopropylsilyl)oxy)pyrrolidine-2-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: 96.0%

triisopropylsilyl chloride (13154-24-0) + (2S,4R)-1-benzyl-4-hydroxyproline methyl ester (114676-48-1) → (2S,4R)-methyl 1-benzyl-4-((triisopropylsilyl)oxy)pyrrolidine-2-carboxylate (882990-54-7)

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; for 20h;

DOI:10.1021/ja510475n

Reference yield:

4R-4-hydroxyproline (51-35-4,30724-02-8) → (2S,4R)-methyl 1-benzyl-4-((triisopropylsilyl)oxy)pyrrolidine-2-carboxylate (882990-54-7)

Guidance literature:

Multi-step reaction with 3 steps

1: SOCl₂ / 72 h / 20 °C

2: Et₃N / CH₂Cl₂ / 5 h / Heating

3: DMAP / CH₂Cl₂ / 12 h / 20 °C

With dmap; thionyl chloride; triethylamine; In dichloromethane;

DOI:10.1016/j.tet.2005.11.070

Reference yield:

(R)-4-hydroxy-L-proline ethyl ester (1499-56-5,775275-31-5,790644-51-8,754962-86-2) → (2S,4R)-methyl 1-benzyl-4-((triisopropylsilyl)oxy)pyrrolidine-2-carboxylate (882990-54-7)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / 5 h / Heating

2: DMAP / CH₂Cl₂ / 12 h / 20 °C

With dmap; triethylamine; In dichloromethane;

DOI:10.1016/j.tet.2005.11.070

upstream raw materials:

triisopropylsilyl chloride

(2S,4R)-1-benzyl-4-hydroxyproline methyl ester

(R)-4-hydroxy-L-proline ethyl ester

4R-4-hydroxyproline

Downstream raw materials:

(2S,4R)-2-{1-benzyl-4-[(triisopropylsilyl)oxy]-pyrrolidinyl}methanol