(S)-3-[(4-Iodo-benzoyl)-methyl-amino]-pyrrolidine-1-carboxylic acid methyl-((R)-1-methyl-pyrrolidin-3-yl)-amide

Base Information

• Chemical Name: (S)-3-[(4-Iodo-benzoyl)-methyl-amino]-pyrrolidine-1-carboxylic acid methyl-((R)-1-methyl-pyrrolidin-3-yl)-amide
• CAS No.: 862847-08-3
• Molecular Formula: C₁₉H₂₇IN₄O₂
• Molecular Weight: 470.353
• Mol file: 862847-08-3.mol

Synonyms:(S)-3-[(4-Iodo-benzoyl)-methyl-amino]-pyrrolidine-1-carboxylic acid methyl-((R)-1-methyl-pyrrolidin-3-yl)-amide

Chemical Property of (S)-3-[(4-Iodo-benzoyl)-methyl-amino]-pyrrolidine-1-carboxylic acid methyl-((R)-1-methyl-pyrrolidin-3-yl)-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-[(4-Iodo-benzoyl)-methyl-amino]-pyrrolidine-1-carboxylic acid methyl-((R)-1-methyl-pyrrolidin-3-yl)-amide

There total 9 articles about (S)-3-[(4-Iodo-benzoyl)-methyl-amino]-pyrrolidine-1-carboxylic acid methyl-((R)-1-methyl-pyrrolidin-3-yl)-amide 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: 83.0%

4-iodobenzoic acid (619-58-9) + (S)-3-Methylamino-pyrrolidine-1-carboxylic acid methyl-((R)-1-methyl-pyrrolidin-3-yl)-amide (762287-56-9) → (S)-3-[(4-Iodo-benzoyl)-methyl-amino]-pyrrolidine-1-carboxylic acid methyl-((R)-1-methyl-pyrrolidin-3-yl)-amide (862847-08-3)

Guidance literature:

With TEA; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 20 ℃; for 20h;

DOI:10.1016/j.bmcl.2005.05.015

Reference yield:

(R)-3-Hydroxy-pyrrolidine-1-carboxylic acid ((R)-1-benzyl-pyrrolidin-3-yl)-methyl-amide (862847-07-2) → (S)-3-[(4-Iodo-benzoyl)-methyl-amino]-pyrrolidine-1-carboxylic acid methyl-((R)-1-methyl-pyrrolidin-3-yl)-amide (862847-08-3)

Guidance literature:

Multi-step reaction with 7 steps

1: TEA / tetrahydrofuran / 18 h / 5 - 20 °C

2: tetrahydrofuran; H₂O / 18 h / 50 °C

3: tetrahydrofuran / 0.5 h / 20 °C

4: 100 percent / H₂ / Pd(OH)2/C / ethanol / 17 h / 20 °C / 2068.59 Torr

5: 89 percent / aq. NaBH(OAc)3 / 1,2-dichloro-ethane / 4 h / 20 °C

6: 100 percent / TFA / CH₂Cl₂ / 1 h / 20 °C

7: 83 percent / EDC; HOBT; TEA / CH₂Cl₂ / 20 h / 20 °C

With TEA; hydrogen; sodium tris(acetoxy)borohydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; 1,2-dichloro-ethane;

DOI:10.1016/j.bmcl.2005.05.015

Reference yield:

4-Nitro-benzenesulfonic acid (R)-1-[((R)-1-benzyl-pyrrolidin-3-yl)-methyl-carbamoyl]-pyrrolidin-3-yl ester → (S)-3-[(4-Iodo-benzoyl)-methyl-amino]-pyrrolidine-1-carboxylic acid methyl-((R)-1-methyl-pyrrolidin-3-yl)-amide (862847-08-3)

Guidance literature:

Multi-step reaction with 6 steps

1: tetrahydrofuran; H₂O / 18 h / 50 °C

2: tetrahydrofuran / 0.5 h / 20 °C

3: 100 percent / H₂ / Pd(OH)2/C / ethanol / 17 h / 20 °C / 2068.59 Torr

4: 89 percent / aq. NaBH(OAc)3 / 1,2-dichloro-ethane / 4 h / 20 °C

5: 100 percent / TFA / CH₂Cl₂ / 1 h / 20 °C

6: 83 percent / EDC; HOBT; TEA / CH₂Cl₂ / 20 h / 20 °C

With TEA; hydrogen; sodium tris(acetoxy)borohydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; 1,2-dichloro-ethane;

DOI:10.1016/j.bmcl.2005.05.015

upstream raw materials:

4-iodobenzoic acid

(S)-3-Methylamino-pyrrolidine-1-carboxylic acid methyl-((R)-1-methyl-pyrrolidin-3-yl)-amide

(R)-3-Hydroxy-pyrrolidine-1-carboxylic acid ((R)-1-benzyl-pyrrolidin-3-yl)-methyl-amide

(3R)-1-benzyl-N-methylpyrrolidin-3-amine