(S)-(+)-rolipram

Base Information

• Chemical Name: (S)-(+)-rolipram
• CAS No.: 85416-73-5
• Molecular Formula: C16H21NO3
• Molecular Weight: 275.348
• Hs Code.: 2933790090
• UNII: H6G4VMQ24K
• DSSTox Substance ID: DTXSID30234634
• Nikkaji Number: J523.412C
• Wikidata: Q27094526
• Pharos Ligand ID: JYQSQFGGZ4LK
• Metabolomics Workbench ID: 60676
• ChEMBL ID: CHEMBL325795
• Mol file: 85416-73-5.mol

Synonyms:(S)-(+)-rolipram;85416-73-5;S-(+)-Rolipram;(S)-ROLIPRAM;S- (+)-Rolipram;(+)-rolipram;(4S)-4-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]PYRROLIDIN-2-ONE;(S)-4-(3-(cyclopentyloxy)-4-methoxyphenyl)pyrrolidin-2-one;Rolipram, (+)-;(4S)-4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-one;UNII-H6G4VMQ24K;H6G4VMQ24K;CHEMBL325795;CHEBI:59540;2-Pyrrolidinone, 4-(3-(cyclopentyloxy)-4-methoxyphenyl)-, (4S)-;(4S)-4-[3-(Cyclopentyloxy)-4-methoxyphenyl]-pyrrolidin-2-one;S-rolipram;1oyn;1xn0;D02FZD;ROLIPRAM, (S)-;MLS006011228;(+)-Rolipram;(S)-Rolipram;SCHEMBL5321568;AMY6779;DTXSID30234634;HMS3267P21;HMS3412I08;HMS3676I08;HMS3884B09;HY-B0392;BDBM50042056;HB2897;MFCD03093861;s2127;AKOS024456541;CCG-267201;DB03606;NCGC00381709-02;NCGC00381709-04;AS-56538;SMR004702988;BCP0726000229;R0183;SW219244-1;F13078;AB01274743-01;AB01274743_02;A923531;BRD-K65856711-001-01-0;Q27094526;(4S)-4-[3-(Cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2 -one;(S)-(+)-4-[3-(Cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one;(4S)-4-(3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL)-2-PYRROLIDINONE;2-PYRROLIDINONE, 4-(3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL)-, (S)-

Chemical Property of (S)-(+)-rolipram

Chemical Property:

• Melting Point: 133-136oC
• PSA: 47.56000
• Density: 1.155
• LogP: 2.94890
• Storage Temp.: Store at RT
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 275.15214353
• Heavy Atom Count: 20
• Complexity: 341

Purity/Quality:

98%,99%, ^*data from raw suppliers

S-(+)-Rolipram ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2CC(=O)NC2)OC3CCCC3
• Isomeric SMILES: COC1=C(C=C(C=C1)[C@@H]2CC(=O)NC2)OC3CCCC3
• Uses: S-(+)-Rolipram inhibits human monocyte cyclic AMP-specific PDE4 with IC50 of 0.75 μM, has anti-inflammatory and anti-depressant activity in the central nervous system, less potent than its R enantiomer S-(+)-Rolipram is an inhibitor of cyclic AMP-specific phosphodiesterase. It is the S isomer of (±)-Rolipram (R640040). Potent PDE4 inhibitor

Technology Process of (S)-(+)-rolipram

There total 56 articles about (S)-(+)-rolipram 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%

(S)-S-benzyl 3-(3-(cyclopentyloxy)-4-methoxyphenyl)-4-nitrobutanethioate (1259130-31-8) → (S)-rolipram (85416-73-5)

Guidance literature:

(S)-S-benzyl 3-(3-(cyclopentyloxy)-4-methoxyphenyl)-4-nitrobutanethioate; With chloro-trimethyl-silane; zinc; In ethanol; at 0 - 20 ℃; for 0.333333h;

With water; sodium hydrogencarbonate; In ethanol; at 20 ℃;

DOI:10.1002/asia.201000540

Reference yield: 82.0%

(3R,4S)-methyl 4-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-oxopyrrolidine-3-carboxylate → (S)-rolipram (85416-73-5)

Guidance literature:

(3R,4S)-methyl 4-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-oxopyrrolidine-3-carboxylate; With hydrogenchloride; lithium hydroxide; In water;

In toluene; for 12h; Reflux;

DOI:10.1021/acscatal.5b00685

Reference yield: 81.0%

(S)-methyl 2-carbomethoxy-4-nitro-3-(3-cyclopentyloxy-4-methoxyphenyl)butyrate → (S)-rolipram (85416-73-5)

Guidance literature:

With palladium on activated carbon; hydrogen; In o-xylene; at 130 ℃; for 18h; under 7500.75 Torr;

DOI:10.1002/anie.201403049

upstream raw materials:

4-Amino-3-(3-cyclopentyloxy-4-methoxy-phenyl)-butyric acid methyl ester

(+/-)-1-Benzyl-4-(3-cyclopentyloxy-4-methoxyphenyl)-pyrrolidin-2-one

Rolipram

N-[2-(3-cyclopentyloxy-4-methoxy-phenyl)-ethyl]-2-diazo-N-(1-methyl-1-phenyl-ethyl)-acetamide

Downstream raw materials:

(S)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-methylpyrrolidin-2-one

Refernces

• 1、 Nagy, Bence S.,Llanes, Patricia,Pericas, Miquel A.,Kappe, C. Oliver,?tv?s, Sándor B.. "Enantioselective Flow Synthesis of Rolipram Enabled by a Telescoped Asymmetric Conjugate Addition-Oxidative Aldehyde Esterification Sequence Using in Situ-Generated Persulfuric Acid as Oxidant". . . Retrieved 2022/02/05.
• 2、 -. "Synthesis method of flurolipram". Paragraph 0089-0102. . Retrieved 2021/03/13.