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

Base Information

• Chemical Name: (R)-3-Hydroxy-pyrrolidine-1-carboxylic acid ((R)-1-benzyl-pyrrolidin-3-yl)-methyl-amide
• CAS No.: 862847-07-2
• Molecular Formula: C₁₇H₂₅N₃O₂
• Molecular Weight: 303.404
• Mol file: 862847-07-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (R)-3-Hydroxy-pyrrolidine-1-carboxylic acid ((R)-1-benzyl-pyrrolidin-3-yl)-methyl-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: 77.0%

(R)-1-benzyl-3-[N-(4-nitrophenoxycarbonyl)-N-methylamino]pyrrolidine hydrochloride + (R)-3-hydroxypyrrolidine hydrochloride (104706-47-0,111810-68-5) → (R)-3-Hydroxy-pyrrolidine-1-carboxylic acid ((R)-1-benzyl-pyrrolidin-3-yl)-methyl-amide (862847-07-2)

Guidance literature:

With TEA; In N,N-dimethyl-formamide; at 70 ℃; for 18h;

DOI:10.1016/j.bmcl.2005.05.015

Reference yield:

(3R)-1-benzyl-N-methylpyrrolidin-3-amine (144043-17-4) → (R)-3-Hydroxy-pyrrolidine-1-carboxylic acid ((R)-1-benzyl-pyrrolidin-3-yl)-methyl-amide (862847-07-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / tetrahydrofuran / 3 h / 5 - 20 °C

2: 77 percent / TEA / dimethylformamide / 18 h / 70 °C

With TEA; In tetrahydrofuran; N,N-dimethyl-formamide;

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-{[5-(2-Chloro-phenyl)-thiophene-2-carbonyl]-methyl-amino}-pyrrolidine-1-carboxylic acid methyl-((R)-1-methyl-pyrrolidin-3-yl)-amide

Guidance literature:

Multi-step reaction with 8 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: 77 percent / EDC; HOBT; TEA / CH₂Cl₂ / 20 h / 20 °C

8: Pd(PPh₃)4; aq. Na₂CO₃ / dioxane / 12 h / Heating

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; TEA; hydrogen; sodium tris(acetoxy)borohydride; sodium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; 1,2-dichloro-ethane; 8: Suzuki coupling;

DOI:10.1016/j.bmcl.2005.05.015

upstream raw materials:

(R)-3-hydroxypyrrolidine hydrochloride

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

Downstream raw materials:

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