(2R)-1-(Phenylmethyl)-N-[3-(spiro[isobenzofuran-1(3H),4'-piperidin]-1-yl)propyl-2-pyrrolidinecarboxamide

Base Information

• Chemical Name: (2R)-1-(Phenylmethyl)-N-[3-(spiro[isobenzofuran-1(3H),4'-piperidin]-1-yl)propyl-2-pyrrolidinecarboxamide
• CAS No.: 475150-69-7
• Molecular Formula: C27H35N3O2.2HCl
• Molecular Weight: 433.58600

Synonyms:(2R)-1-(Phenylmethyl)-N-(3-spiro[isobenzofuran-1(3H),4'-piperidin]-1'-ylpropyl)-2-pyrrolidinecarboxamide;2-Pyrrolidinecarboxamide, 1-(phenylmethyl)-N-(3-spiro[isobenzofuran-1(3H),4'-piperidin]-1'-ylpropyl)-, (2R)-;

Chemical Property of (2R)-1-(Phenylmethyl)-N-[3-(spiro[isobenzofuran-1(3H),4'-piperidin]-1-yl)propyl-2-pyrrolidinecarboxamide

Chemical Property:

• PSA: 44.81000
• Density: 1.19
• LogP: 3.94550
• Storage Temp.: Desiccate at RT
• Solubility.: Soluble in DMSO

Purity/Quality:

99%, ^*data from raw suppliers

BAN ORL 24 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: BAN ORL 24 is a KOR-3 (NOP) antagonist.

Technology Process of (2R)-1-(Phenylmethyl)-N-[3-(spiro[isobenzofuran-1(3H),4'-piperidin]-1-yl)propyl-2-pyrrolidinecarboxamide

There total 6 articles about (2R)-1-(Phenylmethyl)-N-[3-(spiro[isobenzofuran-1(3H),4'-piperidin]-1-yl)propyl-2-pyrrolidinecarboxamide 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: 62.3%

N-[3-spiro[isobenzofuran-1(3H),4'-piperidine]-1-ylpropyl]-D-prolineamide (788152-33-0) + benzaldehyde (100-52-7) → (D)-1-benzylpyrrolidine-2-carboxylic acid{3-[spiro(isobenzofuran-1(3H),4'-piperidine)-1'-yl]propyl}amide (475150-69-7)

Guidance literature:

With sodium tris(acetoxy)borohydride; In chloroform; at 20 ℃; for 1h;

DOI:10.1021/jm0509851

Reference yield: 37.0%

(D)-1-benzylpyrrolidine-2-carboxylic acid (56080-99-0) + 3-spiro[isobenzofuran-1(3H),4'-piperidine]-1-ylpropane-1-amine (252002-17-8) → (D)-1-benzylpyrrolidine-2-carboxylic acid{3-[spiro(isobenzofuran-1(3H),4'-piperidine)-1'-yl]propyl}amide (475150-69-7)

Guidance literature:

(D)-1-benzylpyrrolidine-2-carboxylic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 0 ℃; for 0.166667h;

3-spiro[isobenzofuran-1(3H),4'-piperidine]-1-ylpropane-1-amine; In N,N-dimethyl-formamide; for 24h;

DOI:10.1016/j.bmc.2009.05.068

Reference yield:

2-(3-spiro[isobenzofuran-1(3H),4'-piperidine-1-yl]propyl)-1H-indole-1,3(2H)-dione (475152-12-6) → (D)-1-benzylpyrrolidine-2-carboxylic acid{3-[spiro(isobenzofuran-1(3H),4'-piperidine)-1'-yl]propyl}amide (475150-69-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 85.8 percent / hydrazine monohydrate / ethanol; CHCl₃ / 1 h / Heating

2.1: HOBT; WSC / CHCl₃ / 0.08 h / 20 °C

2.2: 83.2 percent / CHCl₃ / 0.5 h / 20 °C

3.1: 88.7 percent / H₂ / Pd(OH)2 / methanol / 1 h

4.1: 62.3 percent / NaBH(OAc)3 / CHCl₃ / 1 h / 20 °C

With hydrogen; sodium tris(acetoxy)borohydride; benzotriazol-1-ol; hydrazine hydrate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium dihydroxide; In methanol; ethanol; chloroform;

DOI:10.1021/jm0509851

upstream raw materials:

N-[3-spiro[isobenzofuran-1(3H),4'-piperidine]-1-ylpropyl]-D-prolineamide

benzaldehyde

2-(3-spiro[isobenzofuran-1(3H),4'-piperidine-1-yl]propyl)-1H-indole-1,3(2H)-dione

1-benzyloxycarbonyl-N-[3-spiro[isobenzofuran-1(3H),4'-piperidine]-1-ylpropyl]-D-prolineamide

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