3-(Aminomethyl)-5-methylhexanoic acid

Base Information

• Chemical Name: 3-(Aminomethyl)-5-methylhexanoic acid
• CAS No.: 128013-69-4
• Molecular Formula: C₈H₁₇NO₂
• Molecular Weight: 159.228
• DSSTox Substance ID: DTXSID20861392
• Nikkaji Number: J258.872B
• ChEMBL ID: CHEMBL88034
• Mol file: 128013-69-4.mol

Synonyms:(R-)-3-isobutyl GABA;(S)-3-(aminomethyl)-5-methylhexanoic acid;(S+)-3-isobutyl GABA;1008, CI;3 isobutyl GABA;3-(aminomethyl)-5-methylhexanoic acid;3-isobutyl GABA;CI 1008;CI-1008;CI1008;GABA, 3-isobutyl;Lyrica;pregabalin

Chemical Property of 3-(Aminomethyl)-5-methylhexanoic acid

Chemical Property:

• Appearance/Colour: white powder
• Melting Point: 148-150 °C
• Boiling Point: 274.032 °C at 760 mmHg
• PKA: 4.23±0.10(Predicted)
• Flash Point: 119.53 °C
• PSA: 63.32000
• Density: 0.997 g/cm³
• LogP: 1.78240
• Storage Temp.: -20°C Freezer
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 159.125928785
• Heavy Atom Count: 11
• Complexity: 123

Purity/Quality:

99% ^*data from raw suppliers

rac-pregabalin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(CC(=O)O)CN
• Uses: As a GABA analogue, 3-(Aminomethyl)-5-methylhexanoic acid can be used as an anticonvulsant. Controlled substance in the United States.

Technology Process of 3-(Aminomethyl)-5-methylhexanoic acid

There total 84 articles about 3-(Aminomethyl)-5-methylhexanoic acid 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: 97.0%

5-methyl-3-(nitromethyl)hexanoic acid (181289-21-4) → (R,S)-3-iso-butyl-4-aminobutyric acid (128013-69-4,130912-52-6,148553-50-8,148553-51-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 25 ℃; for 24h; under 760.051 Torr;

DOI:10.1039/d0nj02263b

Reference yield: 95.0%

t-butyl 4-(2-methylpropyl)-2-oxopyrrolidine-1-carboxylate (1373869-02-3) → (R,S)-3-iso-butyl-4-aminobutyric acid (128013-69-4,130912-52-6,148553-50-8,148553-51-9)

Guidance literature:

t-butyl 4-(2-methylpropyl)-2-oxopyrrolidine-1-carboxylate; With sodium hydroxide; In methanol; for 1h; Reflux; Large scale;

With hydrogenchloride; In dichloromethane; water; at 20 ℃; for 0.5h; Large scale;

Reference yield: 89.0%

(±)?3?(carbamoylmethyl)?5?methylhexanoic acid (181289-15-6) → (R,S)-3-iso-butyl-4-aminobutyric acid (128013-69-4,130912-52-6,148553-50-8,148553-51-9)

Guidance literature:

With bromine; sodium hydroxide; In water; at 0 - 85 ℃; for 3h; Temperature; Large scale;

upstream raw materials:

4-methylpent-2-enal

5-methyl-(2-ethylcarboxy)-3-nitromethylhexanoic acid ethyl ester

3-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-5-methyl-hex-4-enoic acid ethyl ester

3-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-pent-4-enoic acid ethyl ester

Downstream raw materials:

C₈H₈O₃*C₈H₁₇NO₂

(S)-pregabalin-(-)-O,O'-dibenzoyl-L-tartrate

3-(aminomethyl)-5-methylhex-5-enoic acid

3-(aminomethyl)-5-methylhex-4-enoic acid

Refernces

• 1、 Serfass, Lucile,Casara, Patrick J.. "General synthesis of 3-substituted alkenyl GABA as potential anticonvulsants". . p. 2599 - 2602. Retrieved 1998.
• 2、 -. "PROCESS FOR THE PREPARATION OF GAMMA AMINO BUTYRIC ACIDS AND ANALOGS THEREOF". Page/Page column 14-15. . Retrieved 2021/08/20.
• 3、 D'Oca, Caroline Da Ros Montes,Mass, Eduardo Bustos,Ongaratto, Renata Fontes,De Andrade, Arthur Motta,D'Oca, Marcelo G. Montes,Russowsky, Dennis. "Synthesis of (+/-)-Pregabalin and its novel lipophilic β-alkyl-substituted analogues from fatty chains". . p. 13230 - 13239. Retrieved 2020/08/28.