2-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Base Information

• Chemical Name: 2-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
• CAS No.: 905981-10-4
• Molecular Formula: C₂₃H₃₇NO₅Si
• Molecular Weight: 435.636
• Mol file: 905981-10-4.mol

Synonyms:2-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Chemical Property of 2-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

There total 3 articles about 2-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 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%

1-benzyl 2-methyl 2-(3'-hydroxypropyl)pyrrolidine-1,2-dicarboxylate (161417-44-3) + tert-butyldimethylsilyl chloride (18162-48-6) → 2-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (905981-10-4)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/ja061660s

Reference yield:

N-carbobenzyloxy-L-proline methyl ester (5211-23-4) → 2-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (905981-10-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LHMDS / tetrahydrofuran / 0.58 h / -78 °C

1.2: 85 percent / tetrahydrofuran / 2 h / -78 °C

2.1: 9-BBN / tetrahydrofuran / 3 h / 20 °C

2.2: 92 percent / NaOH; H₂O₂ / H₂O / 1 h

3.1: 96 percent / imidazole / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja061660s

Reference yield:

1-Benzyloxycarbonyl-2-(methoxycarbonyl)-2-(2-propenyl)pyrrolidine (161417-43-2) → 2-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (905981-10-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 9-BBN / tetrahydrofuran / 3 h / 20 °C

1.2: 92 percent / NaOH; H₂O₂ / H₂O / 1 h

2.1: 96 percent / imidazole / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja061660s

upstream raw materials:

1-benzyl 2-methyl 2-(3'-hydroxypropyl)pyrrolidine-1,2-dicarboxylate

tert-butyldimethylsilyl chloride

N-carbobenzyloxy-L-proline methyl ester

1-Benzyloxycarbonyl-2-(methoxycarbonyl)-2-(2-propenyl)pyrrolidine

Downstream raw materials:

7-(1-tert-butoxycarbonyl-1H-indol-3-ylmethyl)-8-(4-methoxy-benzyl)-6,9-dioxo-5,8-diaza-tricyclo[5.2.2.0^1,5]undecane-11-carboxylic acid methyl ester