249289-07-4

Basic information

• Product Name: Diethyl 2-(4-octanoylphenethyl)-2-acetamidomalonate
• CAS NO: 249289-07-4
• Molecular Formula: C25H37NO6
• Molecular Weight: 447.572
• Mol File: 249289-07-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Diethyl 2-(4-octanoylphenethyl)-2-acetamidomalonate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl 2-(4-octanoylphenethyl)-2-acetamidomalonate(249289-07-4)
• EPA Substance Registry System: Diethyl 2-(4-octanoylphenethyl)-2-acetamidomalonate(249289-07-4)

Safety Data

• Hazardous Substances Data: 249289-07-4(Hazardous Substances Data)

Usage

General Description

Diethyl 2-(4-octanoylphenethyl)-2-acetamidomalonate is a chemical compound that belongs to the class of acylphenethylamines. It is also known as "Octodrine" and is commonly used as a stimulant and thermogenic agent in various dietary supplements and weight loss products. Octodrine is structurally similar to other stimulants such as ephedrine and amphetamine and is known for its ability to increase energy levels, mental alertness, and focus. However, the use of octodrine has been controversial due to its potential negative side effects and regulatory concerns in some countries. It is important to use octodrine with caution and under the guidance of a healthcare professional due to its potential risks and lack of comprehensive safety data.

Synthetic route

n-octanoic acid chloride (111-64-8) + 2-acetamido-1,3-diacetoxy-2-(2-phenylethyl)propane (162359-95-7) → 2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate (249289-07-4)

Conditions	Yield
With aluminum (III) chloride; 1,2-dichloro-ethane at 0 - 20℃; for 18.5h; Friedel-Crafts Acylation;	81%
With aluminium trichloride In 1,2-dichloro-ethane at 20℃; for 12h; Friedel-Crafts acylation;	64%
Stage #1: n-octanoic acid chloride With aluminum (III) chloride In 1,2-dichloro-ethane at -15 - -10℃; for 1.5h; Inert atmosphere; Stage #2: 2-acetamido-1,3-diacetoxy-2-(2-phenylethyl)propane In 1,2-dichloro-ethane at -15 - 20℃; for 19h; Inert atmosphere;

2-acetylamino-2-phenylethylmalonic acid diethyl ester (5463-92-3) → 2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate (249289-07-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: LiAlH4 / tetrahydrofuran / 2 h / 20 °C 2: pyridine / 16 h / 20 °C 3: 64 percent / AlCl3 / 1,2-dichloro-ethane / 12 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / methanol / 18 h / 0 - 20 °C 2: pyridine / 15 h / 20 °C 3: aluminum (III) chloride; 1,2-dichloro-ethane / 18.5 h / 0 - 20 °C View Scheme

1-phenyl-2-bromoethane (103-63-9) → 2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate (249289-07-4)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium ethoxide / ethanol / 0.5 h / 20 °C 1.2: ethanol / 3 h / 65 °C 2.1: LiAlH4 / tetrahydrofuran / 2 h / 20 °C 3.1: pyridine / 16 h / 20 °C 4.1: 64 percent / AlCl3 / 1,2-dichloro-ethane / 12 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: caesium carbonate / dimethyl sulfoxide / 6 h / 65 °C 2: sodium tetrahydroborate / methanol / 18 h / 0 - 20 °C 3: pyridine / 15 h / 20 °C 4: aluminum (III) chloride; 1,2-dichloro-ethane / 18.5 h / 0 - 20 °C View Scheme

2-acetylaminomalonic acid diethyl ester (1068-90-2) + (+-)-<2-bromo-ethyl>-phenyl-phosphinic acid ethyl ester → 2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate (249289-07-4)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium ethoxide / ethanol / 0.5 h / 20 °C 1.2: ethanol / 3 h / 65 °C 2.1: LiAlH4 / tetrahydrofuran / 2 h / 20 °C 3.1: pyridine / 16 h / 20 °C 4.1: 64 percent / AlCl3 / 1,2-dichloro-ethane / 12 h / 20 °C View Scheme

N-(1-hydroxy-2-(hydroxymethyl)-4-phenylbut-2-yl)acetamide → 2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate (249289-07-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 16 h / 20 °C 2: 64 percent / AlCl3 / 1,2-dichloro-ethane / 12 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: pyridine / 15 h / 20 °C 2: aluminum (III) chloride; 1,2-dichloro-ethane / 18.5 h / 0 - 20 °C View Scheme

2-acetylaminomalonic acid diethyl ester (1068-90-2) → 2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate (249289-07-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: caesium carbonate / dimethyl sulfoxide / 6 h / 65 °C 2: sodium tetrahydroborate / methanol / 18 h / 0 - 20 °C 3: pyridine / 15 h / 20 °C 4: aluminum (III) chloride; 1,2-dichloro-ethane / 18.5 h / 0 - 20 °C View Scheme

2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate (249289-07-4) → 2-acetamido-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol diacetate (162358-09-0)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 2h;	95%
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃;	6.3 g

2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate (249289-07-4) → 1-[4-(3-amino-4-hydroxy-3-hydroxymethyl-butyl)-phenyl]-octan-1-one (249289-08-5)

Conditions	Yield
With lithium hydroxide In tetrahydrofuran; methanol for 3h; Hydrolysis; Heating;	51%

2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate (249289-07-4) → 2-amino-2-{2-[4-(1-hydroxy-octyl)-phenyl]-ethyl}-propane-1,3-diol

Conditions	Yield
Multi-step reaction with 2 steps 1: 51 percent / 2 N aq. LiOH / methanol; tetrahydrofuran / 3 h / Heating 2: 66 percent / NaBH4 / ethanol / 3 h / 20 °C View Scheme

2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate (249289-07-4) → 2-amino-2-[2-[4-(1-hydroxyiminooctyl)phenyl]ethyl]propane-1,3-diol

Conditions	Yield
Multi-step reaction with 2 steps 1: 51 percent / 2 N aq. LiOH / methanol; tetrahydrofuran / 3 h / Heating 2: 25 percent / H2NOH*HCl / ethanol; CHCl3 / 1.5 h / Heating View Scheme

Upstream product

• 111-64-8 n-octanoic acid chloride 
• 162359-95-7 2-acetamido-1,3-diacetoxy-2-(2-phenylethyl)propane 
• 1068-90-2 2-acetylaminomalonic acid diethyl ester 
• 103-63-9 1-phenyl-2-bromoethane 
• 5463-92-3 2-acetylamino-2-phenylethylmalonic acid diethyl ester 

Downstream Products

• 249289-08-5 1-[4-(3-amino-4-hydroxy-3-hydroxymethyl-butyl)-phenyl]-octan-1-one 
• 162358-09-0 2-acetamido-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol diacetate 

Relevant articles and documents

PROCESS FOR PREPARATION OF HIGHLY PURE FINGOLIMOD HYDROCHLORIDE

The present invention provides process for preparation of highly pure Fingolimod hydrochloride (I) having purity of greater than 99.8% (by HPLC),(I) without involving the use of column chromatographic purification in the entire process. Fingolimod hydrochloride (I) obtained by the process of present invention may be useful as active pharmaceutical ingredient in pharmaceutical compositions for the treatment of autoimmune related disorder including multiple sclerosis.

Synthesis and immunosuppressive activity of 2-substituted 2- aminopropane-1,3-diols and 2-aminoethanols

A series of 2-substituted 2-aminopropane-1,3-diols was synthesized and evaluated for their lymphocyte-decreasing effect and immunosuppressive effect on rat skin allograft. A phenyl ring was introduced into the alkyl chain of the lead compound 3, which is an immunosuppressive agent structurally simplified from myriocin (1, ISP-I) via compound 2. The potency of the various compounds was dependent upon the position of the phenyl ring within the alkyl side chain. The most suitable length between the quaternary carbon atom and the phenyl ring was two carbon atoms. 2-Substituted 2-aminoethanols were successively synthesized and evaluated for their T-cell-decreasing effect and immunosuppressive effect using a popliteal lymph node gain assay in rats. The absolute configuration at the quaternary carbon affected the activity, and the (pro-S)-hydroxymethyl group of compound 6 was essential for potent immunosuppressive activity. Favorable substituents for the (pro-R)- hydroxymethyl group of 6 were hydroxyalkyl (hydroxyethyl and hydroxypropyl) or lower alkyl (methyl and ethyl) groups. 2-Amino-2-[2-(4- octylphenyl)ethyl]propane-1,3-diol hydrochloride (6, FTY720) was found to possess considerable activity and is expected to be useful as an immunosuppressive drug for organ transplantation.