(R)-1-benzyloxycarbonyl-3-(t-butyldimethylsilyloxy)pyrrolidine

Base Information

• Chemical Name: (R)-1-benzyloxycarbonyl-3-(t-butyldimethylsilyloxy)pyrrolidine
• CAS No.: 150931-62-7
• Molecular Formula: C₁₈H₂₉NO₃Si
• Molecular Weight: 335.519
• Mol file: 150931-62-7.mol

Synonyms:(R)-1-benzyloxycarbonyl-3-(t-butyldimethylsilyloxy)pyrrolidine

Chemical Property of (R)-1-benzyloxycarbonyl-3-(t-butyldimethylsilyloxy)pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (R)-1-benzyloxycarbonyl-3-(t-butyldimethylsilyloxy)pyrrolidine

There total 2 articles about (R)-1-benzyloxycarbonyl-3-(t-butyldimethylsilyloxy)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: 97.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (3R)-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester (100858-33-1) → (R)-1-benzyloxycarbonyl-3-(t-butyldimethylsilyloxy)pyrrolidine (150931-62-7)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 5h;

DOI:10.1246/bcsj.72.2737

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (R)-1-benzyloxycarbonyl-3-(t-butyldimethylsilyloxy)pyrrolidine (150931-62-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 83.98 g / K₃CO₃ / ethyl acetate; H₂O; cyclohexanol / 0.5 h / 20 °C

2: 97 percent / Et₃N / dimethylformamide / 5 h / 20 °C

With potassium carbonate; triethylamine; In water; ethyl acetate; N,N-dimethyl-formamide; cyclohexanol; 1: Substitution / 2: Silylation;

DOI:10.1246/bcsj.72.2737

Reference yield:

(R)-1-benzyloxycarbonyl-3-(t-butyldimethylsilyloxy)pyrrolidine (150931-62-7) → methyl (2S,4R)-[1-benzoyloxy-4-(t-butyldimethylsilyloxy)pyrrolidin-2-yl]acetate

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / Pd/C / methanol / 2 h / 20 °C

2: 9 percent / H₂O₂; Et₄NCl / Na₂WO₄*2H₂O / CH₂Cl₂; H₂O / 4 h / 0 °C

3: 85 percent / ZnI₂ / CH₂Cl₂ / 1 h / -90 °C

4: AcOH / 14 h / 20 °C

5: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

With tetraethylammonium chloride; hydrogen; dihydrogen peroxide; acetic acid; triethylamine; sodium tungstate; palladium on activated charcoal; zinc(II) iodide; In methanol; dichloromethane; water; 1: Catalytic hydrogenation / 2: Oxidation / 3: Condensation / 4: Desilylation / 5: Esterification;

DOI:10.1246/bcsj.72.2737

upstream raw materials:

tert-butyldimethylsilyl chloride

(3R)-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

benzyl chloroformate

Downstream raw materials:

methyl (2R,4R)-[1-benzoyloxy-4-(t-butyldimethylsilyloxy)pyrrolidin-2-yl]acetate

(2R,4R)-1-benzyloxycarbonyl-4-(t-butyldimethylsilyloxy)-2-(3-chloropropyl)pyrrolidine

(2R,4R)-1-benzyloxycarbonyl-4-(t-butyldimethylsilyloxy)-2-(3-hydroxypropyl)pyrrolidine

(2S,4R)-1-benzoyloxy-4-(t-butyldimethylsilyloxy)-2-[4-(t-butyldimethylsilyloxy)-1-butynyl]pyrrolidine