110958-19-5

Basic information

• Product Name: FASORACETAM
• Synonyms: FASORACETAM;(5R)-5-(piperidine-1-carbonyl)-2-pyrrolidone;(5R)-5-(piperidine-1-carbonyl)pyrrolidin-2-one;(5R)-5-piperidin-1-ylcarbonylpyrrolidin-2-one;2-Pyrrolidinone, 5-(1-piperidinylcarbonyl)-, (5R)-;(5R)-5-(Piperidine-1-Carbonyl)Pyrrolidin-2-One (5R)-5-[Oxo-(1-Piperidyl)Methyl]-2-Pyrrolidinone;aka NS-105;LAM-105)
• CAS NO: 110958-19-5
• Molecular Formula: C₁₀H₁₆N₂O₂
• Molecular Weight: 196.248
• EINECS: 1592732-453-0
• Mol File: 110958-19-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 456.8°Cat760mmHg
• Flash Point: 230.1°C
• Appearance: /
• Density: 1.181g/cm³
• Vapor Pressure: 1.57E-08mmHg at 25°C
• Refractive Index: 1.527
• PKA: 15.45±0.40(Predicted)
• CAS DataBase Reference: FASORACETAM(CAS DataBase Reference)
• NIST Chemistry Reference: FASORACETAM(110958-19-5)
• EPA Substance Registry System: FASORACETAM(110958-19-5)

Safety Data

• Hazardous Substances Data: 110958-19-5(Hazardous Substances Data)

Usage

General Description

Fasoracetam is a synthetic compound that belongs to the racetam family of nootropics, which are known for their cognitive enhancing properties. It is often used as a study aid and to improve memory and learning. Fasoracetam works by modulating the activity of neurotransmitters in the brain, specifically by targeting the glutamate and GABA systems. It is believed to have potential for treating conditions such as ADHD and anxiety, and has shown promise in animal studies for its potential neuroprotective and antidepressant effects. While more research is needed to fully understand its mechanisms and potential therapeutic uses, fasoracetam is considered to be a safe and well-tolerated compound when used at appropriate doses.

InChI:InChI=1/C10H16N2O2/c13-9-5-4-8(11-9)10(14)12-6-2-1-3-7-12/h8H,1-7H2,(H,11,13)/t8-/m1/s1

Synthetic route

piperidine (110-89-4) + L-glutamic acid (56-86-0) → (R)-5-[(piperidin-1-yl)carbonyl]pyrrolidin-2-one (110958-19-5)

Conditions	Yield
With tris(2,2,2-trifluoroethyl) borate for 24h; Reflux; Dean-Stark; Green chemistry; chemoselective reaction;	38%

piperidine (110-89-4) + (2S,5R)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octane-4,8-dione → (R)-5-[(piperidin-1-yl)carbonyl]pyrrolidin-2-one (110958-19-5)

Conditions	Yield
In acetonitrile at 20℃; for 0.166667h;

D-pyrrolidone-5-carboxylic acid (4042-36-8) → (R)-5-[(piperidin-1-yl)carbonyl]pyrrolidin-2-one (110958-19-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: PTSA / toluene / 16 h / Heating 2: acetonitrile / 0.17 h / 20 °C View Scheme

piperidine (110-89-4) + D-pyrrolidone-5-carboxylic acid (4042-36-8) → (R)-5-[(piperidin-1-yl)carbonyl]pyrrolidin-2-one (110958-19-5)

Conditions	Yield
In acetonitrile
In ethyl acetate

(R)-5-[(piperidin-1-yl)carbonyl]pyrrolidin-2-one (110958-19-5) → (R)-1-((pyrrolidin-2-yl)methyl)piperidine (575469-26-0)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 4h; Heating;

(R)-5-[(piperidin-1-yl)carbonyl]pyrrolidin-2-one (110958-19-5) → 1-[(R)-1-((4S,5R)-3,5-Dimethyl-4-phenyl-[1,3,2]oxazaphospholidin-2-yl)-pyrrolidin-2-ylmethyl]-piperidine

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 / tetrahydrofuran / 4 h / Heating 2: toluene / 0.5 h / 70 °C View Scheme

D-tartaric acid (147-71-7) + (R)-5-[(piperidin-1-yl)carbonyl]pyrrolidin-2-one (110958-19-5) → 2((5R)-5-(piperidine-1-carbonyl) pyrrolidin-2-one)*(2S,3S-tartaric acid)

Conditions	Yield
In methanol Milling;

4-amino-benzoic acid (150-13-0) + (R)-5-[(piperidin-1-yl)carbonyl]pyrrolidin-2-one (110958-19-5) → (R)-fasoracetam 4-aminobenzoic acid

Conditions	Yield
In ethyl acetate at 25℃; for 96h; Temperature;	5.63 g

urea (57-13-6) + (R)-5-[(piperidin-1-yl)carbonyl]pyrrolidin-2-one (110958-19-5) → (R)-fasoracetam urea

Conditions	Yield
In melt at 90 - 120℃; for 24h; Temperature; Solvent;

benzene-1,3,5-tricarboxylic acid (554-95-0) + (R)-5-[(piperidin-1-yl)carbonyl]pyrrolidin-2-one (110958-19-5) → (R)-fasoracetam trimesic acid

Conditions	Yield
for 1.5h;

(R)-ibuprofene (51146-57-7) + (R)-5-[(piperidin-1-yl)carbonyl]pyrrolidin-2-one (110958-19-5) → (R)-fasoracetam (R)-ibuprofen

Conditions	Yield
for 1.5h;

benzene-1,2-dicarboxylic acid (88-99-3) + (R)-5-[(piperidin-1-yl)carbonyl]pyrrolidin-2-one (110958-19-5) → (R)-fasoracetam phthalic acid

Conditions	Yield
In ethanol

3,5-dihydroxyphenol (108-73-6) + (R)-5-[(piperidin-1-yl)carbonyl]pyrrolidin-2-one (110958-19-5) → (R)-fasoracetam phloroglucinol

Conditions	Yield
for 1.5h;

methyl galloate (99-24-1) + (R)-5-[(piperidin-1-yl)carbonyl]pyrrolidin-2-one (110958-19-5) → (R)-fasoracetam methyl 3,4,5-trihydroxybenzoate

Conditions	Yield
In ethanol

Ethyl gallate (831-61-8) + (R)-5-[(piperidin-1-yl)carbonyl]pyrrolidin-2-one (110958-19-5) → (R)-fasoracetam di(ethyl gallate)

Conditions	Yield
In water at 20℃; Solvent;

Ethyl gallate (831-61-8) + (R)-5-[(piperidin-1-yl)carbonyl]pyrrolidin-2-one (110958-19-5) → (R)-fasoracetam ethyl gallate

Conditions	Yield
for 1.5h;

6-Hydroxy-2-naphthoic acid (16712-64-4) + (R)-5-[(piperidin-1-yl)carbonyl]pyrrolidin-2-one (110958-19-5) → (R)-fasoracetam 6-hydroxy-2-naphthoic acid

Conditions	Yield
for 1.5h;

(R)-5-[(piperidin-1-yl)carbonyl]pyrrolidin-2-one (110958-19-5) + 4-nitro-benzoic acid (62-23-7) → (R)-fasoracetam di(4-nitrobenzoic acid)

Conditions	Yield
for 1.5h;

indole-3-acetic acid (87-51-4) + (R)-5-[(piperidin-1-yl)carbonyl]pyrrolidin-2-one (110958-19-5) → (R)-fasoracetam 2-indole-3-acetic acid

Conditions	Yield
for 1.5h;

Upstream product

• 110-89-4 piperidine 
• 56-86-0 L-glutamic acid 
• 4042-36-8 D-pyrrolidone-5-carboxylic acid 

Downstream Products

• 575469-26-0 (R)-2-[(piperidin-1-yl)methyl]pyrrolidine 

Relevant articles and documents

SOLID FORMS OF FASORACETAM

The disclosure is directed to cocrystals of fasoracetam, including R-fasoracetam, and various coformers. Crystalline materials comprising fasoracetam, including R-fasoracetam, are also provided. The disclosure further includes pharmaceutical compositions and methods of treatment of the cocrystals and crystalline materials of the disclosure.

Synthesis of chiral diamines using novel 2-trichloromethyloxazolidin-4-one precursors derived from 5-oxo-proline and proline

Efficient syntheses of chiral vicinal diamines derived from (S)-oxo-proline and (S)-proline are described. The novel diastereomerically pure precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo-[3.3.0]-octan-4,8-dione 3 and its enantiomer are readily available by reaction of the inexpensive enantiomers of 5-oxo-proline with chloral. Compound 3 reacts with primary and secondary amines to afford the 5-oxo-prolylamides 4 in quantitative yield. In contrast, the (S)-proline-derived precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one 6 gave (S)-N-formylprolylamides 9 and/or (S)-prolylamides 8 depending on the reaction conditions. Upon reduction with LiAlH4, amides 4 and 9 afforded the proline-derived (S)-2-(alkylaminomethyl)pyrrolidines 1 and (S)-N-methyl-2-(alkylaminomethyl)-pyrrolidines 5 in 70-90% yields.