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

Base Information

• Chemical Name: methyl (2R,4R)-[1-benzoyloxy-4-(t-butyldimethylsilyloxy)pyrrolidin-2-yl]acetate
• CAS No.: 150931-56-9
• Molecular Formula: C₂₀H₃₁NO₅Si
• Molecular Weight: 393.555
• Mol file: 150931-56-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about methyl (2R,4R)-[1-benzoyloxy-4-(t-butyldimethylsilyloxy)pyrrolidin-2-yl]acetate 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: 48.0%

benzoyl chloride (98-88-4) + [4-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-pyrrolidin-2-yl]-acetic acid methyl ester → methyl (2R,4R)-[1-benzoyloxy-4-(t-butyldimethylsilyloxy)pyrrolidin-2-yl]acetate (150931-56-9) + methyl (2S,4R)-[1-benzoyloxy-4-(t-butyldimethylsilyloxy)pyrrolidin-2-yl]acetate

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1246/bcsj.72.2737

Reference yield:

ketene t-butyldimethylsilyl methyl acetal (77086-38-5) + benzoyl chloride (98-88-4) + (4R)-4-(t-butyldimethylsilyloxy)-1-pyrroline N-oxide (150931-64-9) → methyl (2R,4R)-[1-benzoyloxy-4-(t-butyldimethylsilyloxy)pyrrolidin-2-yl]acetate (150931-56-9) + methyl (2S,4R)-[1-benzoyloxy-4-(t-butyldimethylsilyloxy)pyrrolidin-2-yl]acetate

Guidance literature:

benzoyl chloride; (4R)-4-(t-butyldimethylsilyloxy)-1-pyrroline N-oxide; In dichloromethane; at 0 ℃; for 5.55556E-05h; Flow reactor;

ketene t-butyldimethylsilyl methyl acetal; In dichloromethane; at 0 ℃; for 0.00109167h; Overall yield = 74 percent; Overall yield = 0.490 g; Flow reactor;

DOI:10.1055/s-0039-1691601

Reference yield:

O1-benzyl O2-methyl (2S,4R)-4-[tert-butyl(dimethyl)silyl]oxypyrrolidine-1,2-dicarboxylate (114358-14-4) → methyl (2R,4R)-[1-benzoyloxy-4-(t-butyldimethylsilyloxy)pyrrolidin-2-yl]acetate (150931-56-9)

Guidance literature:

Multi-step reaction with 7 steps

1: H₂ / Pd/C / methanol / 1 h / 20 °C

2: 30 percent H₂O₂; SeO₂ / acetone / 0.67 h / 10 - 15 °C

3: 960 mg / NaOH / methanol; H₂O / 1 h / 20 °C

4: 69 percent / H₂O₂; Et₄NCl; K₂CO₃ / Na₂WO₄*2H₂O / CH₂Cl₂; H₂O

5: 85 percent / ZnI₂ / CH₂Cl₂ / 1 h / -90 °C

6: AcOH / 14 h / 20 °C

7: 48 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

With sodium hydroxide; selenium(IV) oxide; tetraethylammonium chloride; hydrogen; dihydrogen peroxide; potassium carbonate; acetic acid; triethylamine; sodium tungstate; palladium on activated charcoal; zinc(II) iodide; In methanol; dichloromethane; water; acetone; 1: Catalytic hydrogenation / 2: Oxidation / 3: Hydrolysis / 4: Oxidation / 5: Condensation / 6: Desilylation / 7: Esterification;

DOI:10.1246/bcsj.72.2737

upstream raw materials:

benzoyl chloride

O₁-benzyl O₂-methyl (2S,4R)-4-[tert-butyl(dimethyl)silyl]oxypyrrolidine-1,2-dicarboxylate

(R)-3-[(1,1-dimethylethyl)dimethylsilyloxy]-pyrrolidine

(4R)-4-(t-butyldimethylsilyloxy)-1-pyrroline N-oxide