N-(2-(trimethylsilyl)ethoxymethyl)-N-[2-iodo-4-methoxyphenyl]-1-{tert-butyloxycarbonyl}pyrrolidine-3-carboxamide

Base Information

• Chemical Name: N-(2-(trimethylsilyl)ethoxymethyl)-N-[2-iodo-4-methoxyphenyl]-1-{tert-butyloxycarbonyl}pyrrolidine-3-carboxamide
• CAS No.: 862885-17-4
• Molecular Formula: C₂₃H₃₇IN₂O₅Si
• Molecular Weight: 576.547
• Mol file: 862885-17-4.mol

Synonyms:N-(2-(trimethylsilyl)ethoxymethyl)-N-[2-iodo-4-methoxyphenyl]-1-{tert-butyloxycarbonyl}pyrrolidine-3-carboxamide

Chemical Property of N-(2-(trimethylsilyl)ethoxymethyl)-N-[2-iodo-4-methoxyphenyl]-1-{tert-butyloxycarbonyl}pyrrolidine-3-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(2-(trimethylsilyl)ethoxymethyl)-N-[2-iodo-4-methoxyphenyl]-1-{tert-butyloxycarbonyl}pyrrolidine-3-carboxamide

There total 5 articles about N-(2-(trimethylsilyl)ethoxymethyl)-N-[2-iodo-4-methoxyphenyl]-1-{tert-butyloxycarbonyl}pyrrolidine-3-carboxamide 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: 100.0%

N-(2-iodo-4-methoxyphenyl)-1-{tert-butyloxycarbonyl}pyrrolidine-3-carboxamide (862885-09-4) + (2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → N-(2-(trimethylsilyl)ethoxymethyl)-N-[2-iodo-4-methoxyphenyl]-1-{tert-butyloxycarbonyl}pyrrolidine-3-carboxamide (862885-17-4)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1021/ol051095i

Reference yield:

1-benzylpyrrolidine-3-carboxylic acid methyl ester (17012-21-4) → N-(2-(trimethylsilyl)ethoxymethyl)-N-[2-iodo-4-methoxyphenyl]-1-{tert-butyloxycarbonyl}pyrrolidine-3-carboxamide (862885-17-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / H₂ / Pd(OH)2/C / ethyl acetate / 8 h / 20 °C

2: 95 percent / NaOH / methanol; H₂O / 2 h / 20 °C

3: 94 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 12 h / 20 °C

4: 66 percent / Et₃Al / toluene / 12 h / 80 °C

5: 100 percent / NaH / tetrahydrofuran / 3 h / 20 °C

With sodium hydroxide; hydrogen; triethylaluminum; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium dihydroxide; In tetrahydrofuran; methanol; water; ethyl acetate; toluene; benzene;

DOI:10.1021/ol051095i

Reference yield:

benzyl 1-{tert-butyloxycarbonyl}pyrrolidine-3-carboxylate (862885-08-3) → N-(2-(trimethylsilyl)ethoxymethyl)-N-[2-iodo-4-methoxyphenyl]-1-{tert-butyloxycarbonyl}pyrrolidine-3-carboxamide (862885-17-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / Et₃Al / toluene / 12 h / 80 °C

2: 100 percent / NaH / tetrahydrofuran / 3 h / 20 °C

With triethylaluminum; sodium hydride; In tetrahydrofuran; toluene;

DOI:10.1021/ol051095i

upstream raw materials:

N-(2-iodo-4-methoxyphenyl)-1-{tert-butyloxycarbonyl}pyrrolidine-3-carboxamide

(2-trimethylethylsilylethoxy)methyl chloride

benzyl 1-{tert-butyloxycarbonyl}pyrrolidine-3-carboxylate

1-benzylpyrrolidine-3-carboxylic acid methyl ester

Downstream raw materials:

5-methoxy-2-oxo-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-1'-carboxylic acid tert-butyl ester

5-methoxy-2-oxo-1-(2-(trimethylsilanyl)ethoxymethyl)-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-1'-carboxylic acid tert-butyl ester