181289-33-8

Basic information

• Product Name: (R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid
• Synonyms: (r)-(-)-3-(2-amino-2-oxoethyl)-5-methylhexanoic acid;(r)-(-)-3-carbamoymethyl-5-methylhexanoic acid;INTERMEDIATE OF PREGABALIN;(R)-3-(2-AMINO-2-OXOETHYL)-5-METHYLHEXANOIC ACID:99+%;3-CarbaMoyl Mehyl-5-Methyl Hexanoic Acid;(3R)-3-(2-AMino-2-oxoethyl)-5-Methylhexanoic Acid;Pregabalin IMpurity III;Hexanoic acid,3-(2-aMino-2-oxoethyl)-5-Methyl-,(3R)-
• CAS NO: 181289-33-8
• Molecular Formula: C₉H₁₇NO₃
• Molecular Weight: 187.23618
• EINECS: 1308068-626-2
• Product Categories: intermidiate of Pregablin;Starting Raw Materials & Intermediates;Aliphatics, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 181289-33-8.mol
• Article Data: 23

Chemical Properties

• Melting Point: 128-133°C
• Boiling Point: 401.929 °C at 760 mmHg
• Flash Point: 196.88 °C
• Appearance: /
• Density: 1.081 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.475
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.68±0.10(Predicted)
• CAS DataBase Reference: (R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid(181289-33-8)
• EPA Substance Registry System: (R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid(181289-33-8)

Safety Data

• Hazardous Substances Data: 181289-33-8(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 181289-33-8 differently. You can refer to the following data:
1. (R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid is a useful chemical intermediate for manufacturing of the anticonvulsant drug, Pregabalin1, 2.
2. An Impurity of the anti-convulsant (S)-Pregabalin (P704790).

Sources

https://quod.lib.umich.edu/a/ark/5550190.0011.a22?rgn=main;view=fulltext https://www.researchgate.net/publication/269660675_Synthesis_and_characterization_of_impurities_of_an_anticonvulsant_drug_Pregabalin

Chemical Properties

White Solid

InChI:InChI=1/C9H17NO3/c1-6(2)3-7(4-8(10)11)5-9(12)13/h6-7H,3-5H2,1-2H3,(H2,10,11)(H,12,13)/t7-/m1/s1

Synthetic route

1‐phenylethan‐1‐amine 3‐(carbamoylmethyl)‐5‐methylhexanoate → (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid (181289-33-8)

Conditions	Yield
Stage #1: 1‐phenylethan‐1‐amine 3‐(carbamoylmethyl)‐5‐methylhexanoate With hydrogenchloride In water at 10 - 30℃; for 2h; pH=0.5 - 2; Stage #2: With sulfuric acid In water at 6 - 40℃; for 3h; pH=1.5; Temperature; Reagent/catalyst; Solvent;	100%

3-isobutylglutarimide → (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid (181289-33-8)

Conditions	Yield
With water In tetrahydrofuran at 45℃; for 15h; Reagent/catalyst; Solvent; Temperature;	96.1%

(3S)-3-(2-(allyloxy)-2-oxoethyl)-5-methylhexanoic acid (1403953-91-2) → (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid (181289-33-8)

Conditions	Yield
Stage #1: (3S)-3-(2-(allyloxy)-2-oxoethyl)-5-methylhexanoic acid With magnesium nitride In methanol at 20 - 80℃; for 16h; Stage #2: With hydrogenchloride In methanol; water pH=3 - 4;	93%

(±)‑3‑(carbamoylmethyl)‑5‑methylhexanoic acid (181289-15-6) → (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid (181289-33-8)

Conditions	Yield
With D-phenylglycine butyl ester In isopropyl alcohol Heating;	90.39%
With (R)-1-phenyl-ethyl-amine In methanol; chloroform at 25 - 40℃; for 3.16h; Solvent; Temperature;	41%
Stage #1: (±)‑3‑(carbamoylmethyl)‑5‑methylhexanoic acid With (R)-1-phenyl-ethyl-amine In ethanol; chloroform for 0.75h; Reflux; Stage #2: With hydrogenchloride In ethanol; chloroform; water for 0.75h; Cooling;	40%

(-)-3-cyclohexylsulfanylcarbonylmethyl-5-methyl-hexanoic acid (1237492-10-2) → (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid (181289-33-8)

Conditions	Yield
With ammonia In water at 40℃;	88%

(3S)-3-(2-ethoxy-2-oxoethyl)-5-methylhexanoic acid (1082077-07-3) → (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid (181289-33-8)

Conditions	Yield
Stage #1: (3S)-3-(2-ethoxy-2-oxoethyl)-5-methylhexanoic acid With ammonium iodide; sodium amide In tetrahydrofuran at 20℃; for 4h; Cooling with ice; Green chemistry; Stage #2: With hydrogenchloride In water pH=4 - 5; Reagent/catalyst; Solvent; Green chemistry;	86.7%
With ammonia; calcium chloride In methanol at 55 - 60℃; under 3000.3 - 3375.34 Torr; Autoclave;
With ammonia; calcium chloride In methanol at 25 - 70℃; under 375.038 - 2250.23 Torr; Autoclave;

(3S)-3-(2-methoxy-2-oxoethyl)-5-methylhexanoic acid (181289-25-8) → (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid (181289-33-8)

Conditions	Yield
Stage #1: (3S)-3-(2-methoxy-2-oxoethyl)-5-methylhexanoic acid With ammonia In water at 20 - 80℃; under 760.051 - 1520.1 Torr; for 6 - 92h; Stage #2: With hydrogenchloride In water pH=1 - 3; Product distribution / selectivity;	60%
Stage #1: (3S)-3-(2-methoxy-2-oxoethyl)-5-methylhexanoic acid With ammonia; ammonium chloride In water at 20 - 40℃; for 42.5h; Stage #2: With hydrogenchloride In water pH=4; Product distribution / selectivity;
Stage #1: (3S)-3-(2-methoxy-2-oxoethyl)-5-methylhexanoic acid With ammonia In water; toluene at 20℃; for 88h; Stage #2: With sulfuric acid In water pH=3; Product distribution / selectivity;
With ammonium hydroxide at 25 - 90℃; for 75h; Reagent/catalyst; Temperature;	75 g

(3R)-5-methyl-3-(2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)hexanoic acid (930585-94-7) → (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid (181289-33-8)

Conditions	Yield
Stage #1: (3R)-5-methyl-3-(2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)hexanoic acid With ammonia; water; lithium In tetrahydrofuran at -40℃; for 6 - 10h; Stage #2: With hydrogenchloride In water pH=1.5 - 1.7; Product distribution / selectivity;	59.37%
Stage #1: (3R)-5-methyl-3-(2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)hexanoic acid With ammonia; water; sodium In tetrahydrofuran at -40℃; for 6 - 10h; Stage #2: With hydrogenchloride In water pH=1.5 - 1.7; Product distribution / selectivity;	39.37%
With sulfuric acid In tetrahydrofuran at 25 - 30℃; Product distribution / selectivity;	39%
With palladium 10% on activated carbon; hydrogen In methanol at 30℃; under 7500.75 Torr; for 12h; Autoclave; Industrial scale;

R-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid 1-phenylpropylamine salt (1385049-51-3) → (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid (181289-33-8)

Conditions	Yield
Stage #1: R-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid 1-phenylpropylamine salt With ammonia In water at 80℃; for 5h; Stage #2: With hydrogenchloride In water at 0℃; pH=1;	53%

(R)-methyl 3-(carbamoylmethyl)-5-methylhexanoate → (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid (181289-33-8)

Conditions	Yield
Stage #1: (R)-methyl 3-(carbamoylmethyl)-5-methylhexanoate With hydrogenchloride In water at 20 - 25℃; for 1 - 10h; Stage #2: With sodium hydroxide In water pH=3; Product distribution / selectivity;
Stage #1: (R)-methyl 3-(carbamoylmethyl)-5-methylhexanoate With hydrogenchloride; water at 20 - 25℃; Stage #2: With sodium hydroxide In water pH=3;

methanol (67-56-1) + 3-isobutylglutaric anhydride (185815-59-2) → (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid (181289-33-8)

Conditions	Yield
Stage #1: methanol; 3-isobutylglutaric anhydride With quinidine at -50℃; for 17h; Stage #2: With ammonia In water at 20 - 40℃; for 72h; Stage #3: With hydrogenchloride In water pH=3; Product distribution / selectivity;

(R)-(-)-phenylglycinol salt of (R)-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid (1001296-65-6) → (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid (181289-33-8)

Conditions	Yield
With hydrogenchloride In water at 60 - 62℃;	n/a

(R)-3-(carbamoylmethyl)-5-methylhexanoic acid (R)-(+)-α-phenylethylamine (185815-61-6) → (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid (181289-33-8)

Conditions	Yield
With hydrogenchloride In water at 31℃; pH=1.7;
With hydrogenchloride In water at 20 - 25℃; for 1.47h;
With hydrogenchloride In water pH=1 - 2;	1.21 g

(±)‑3‑(carbamoylmethyl)‑5‑methylhexanoic acid (181289-15-6) → (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid (181289-33-8) + (S)‑3‑carbamoylmethyl‑5‑methylhexanoic acid (181289-34-9)

Conditions	Yield
With (R)-1-phenyl-ethyl-amine Resolution of racemate;

(3S)-3-(2-methoxy-2-oxoethyl)-5-methylhexanoic acid (181289-25-8) → (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid (181289-33-8) + (S)‑3‑carbamoylmethyl‑5‑methylhexanoic acid (181289-34-9)

Conditions	Yield
Stage #1: (3S)-3-(2-methoxy-2-oxoethyl)-5-methylhexanoic acid With ammonia In water at 20℃; for 92h; Stage #2: With hydrogenchloride In water pH=3;

5-methyl-3-carboxymethylhexanoic acid (75143-89-4) → (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid (181289-33-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: urea / 12 h / 130 - 135 °C 1.2: 60 - 90 °C 2.1: chloroform / 0.5 h / 50 - 55 °C 3.1: hydrogenchloride / water / 1.47 h / 20 - 25 °C View Scheme
Multi-step reaction with 4 steps 1.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere 2.1: ammonia / water; tert-butyl methyl ether / 0 - 20 °C 2.2: pH 2 3.1: acetone / water / 80 °C 4.1: ammonia / water / 5 h / 80 °C 4.2: 0 °C / pH 1 View Scheme
Multi-step reaction with 4 steps 1.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere 2.1: ammonia / water; tert-butyl methyl ether / 0 - 20 °C 2.2: pH 2 3.1: chloroform; ethanol / 0.75 h / 60 - 63 °C 4.1: ammonia / water / 5 h / 80 °C 4.2: 0 °C / pH 1 View Scheme

(S)‑3‑carbamoylmethyl‑5‑methylhexanoic acid (181289-34-9) → (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid (181289-33-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid / toluene / Reflux 1.2: 25 - 65 °C 1.3: 1.5 h / 10 - 15 °C 2.1: chloroform / 0.5 h / 50 - 55 °C 3.1: hydrogenchloride / water / 1.47 h / 20 - 25 °C View Scheme

isovaleraldehyde (590-86-3) → (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid (181289-33-8)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: di-n-propylamine; ethyl 2-cyanoacetate / cyclohexane / 2 h / 25 - 30 °C / Reflux 1.2: 5.17 h / 25 - 50 °C 1.3: 48 h / Reflux 2.1: urea / 12 h / 130 - 135 °C 2.2: 60 - 90 °C 3.1: chloroform / 0.5 h / 50 - 55 °C 4.1: hydrogenchloride / water / 1.47 h / 20 - 25 °C View Scheme
Multi-step reaction with 7 steps 1.1: piperidine; pyridine; acetic acid / hexane / 48 h / Reflux; Inert atmosphere 2.1: di-n-propylamine / 16 h / 15 - 55 °C 3.1: hydrogen bromide / water / 72 h / 100 °C 4.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere 5.1: ammonia / water; tert-butyl methyl ether / 0 - 20 °C 5.2: pH 2 6.1: acetone / water / 80 °C 7.1: ammonia / water / 5 h / 80 °C 7.2: 0 °C / pH 1 View Scheme
Multi-step reaction with 7 steps 1.1: piperidine; pyridine; acetic acid / hexane / 48 h / Reflux; Inert atmosphere 2.1: di-n-propylamine / 16 h / 15 - 55 °C 3.1: hydrogen bromide / water / 72 h / 100 °C 4.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere 5.1: ammonia / water; tert-butyl methyl ether / 0 - 20 °C 5.2: pH 2 6.1: chloroform; ethanol / 0.75 h / 60 - 63 °C 7.1: ammonia / water / 5 h / 80 °C 7.2: 0 °C / pH 1 View Scheme

3-isobutylglutaric anhydride (185815-59-2) → (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid (181289-33-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: ammonia / water; tert-butyl methyl ether / 0 - 20 °C 1.2: pH 2 2.1: acetone / water / 80 °C 3.1: ammonia / water / 5 h / 80 °C 3.2: 0 °C / pH 1 View Scheme
Multi-step reaction with 3 steps 1.1: ammonia / water; tert-butyl methyl ether / 0 - 20 °C 1.2: pH 2 2.1: chloroform; ethanol / 0.75 h / 60 - 63 °C 3.1: ammonia / water / 5 h / 80 °C 3.2: 0 °C / pH 1 View Scheme
Multi-step reaction with 4 steps 1.1: 1,4-diaza-bicyclo[2.2.2]octane / tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere 2.1: chloroformic acid ethyl ester; triethylamine / acetone / -20 °C / Inert atmosphere 2.2: 2 h / -20 °C 2.3: 0 °C 3.1: acetone / water / 80 °C 4.1: ammonia / water / 5 h / 80 °C 4.2: 0 °C / pH 1 View Scheme
Multi-step reaction with 4 steps 1.1: 1,4-diaza-bicyclo[2.2.2]octane / tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere 2.1: chloroformic acid ethyl ester; triethylamine / acetone / -20 °C / Inert atmosphere 2.2: 2 h / -20 °C 2.3: 0 °C 3.1: chloroform; ethanol / 0.75 h / 60 - 63 °C 4.1: ammonia / water / 5 h / 80 °C 4.2: 0 °C / pH 1 View Scheme
Multi-step reaction with 2 steps 1: dmap / toluene / -20 - -10 °C / Industrial scale 2: hydrogen; palladium 10% on activated carbon / methanol / 12 h / 30 °C / 7500.75 Torr / Autoclave; Industrial scale View Scheme

diethyl 2-(3-methylbutylidene)malonate (51615-30-6) → (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid (181289-33-8)

Conditions	Yield
Multi-step reaction with 6 steps 1.1: di-n-propylamine / 16 h / 15 - 55 °C 2.1: hydrogen bromide / water / 72 h / 100 °C 3.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere 4.1: ammonia / water; tert-butyl methyl ether / 0 - 20 °C 4.2: pH 2 5.1: acetone / water / 80 °C 6.1: ammonia / water / 5 h / 80 °C 6.2: 0 °C / pH 1 View Scheme
Multi-step reaction with 6 steps 1.1: di-n-propylamine / 16 h / 15 - 55 °C 2.1: hydrogen bromide / water / 72 h / 100 °C 3.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere 4.1: ammonia / water; tert-butyl methyl ether / 0 - 20 °C 4.2: pH 2 5.1: chloroform; ethanol / 0.75 h / 60 - 63 °C 6.1: ammonia / water / 5 h / 80 °C 6.2: 0 °C / pH 1 View Scheme
Multi-step reaction with 7 steps 1.1: di-n-propylamine / 16 h / 15 - 55 °C 2.1: hydrogen bromide / water / 72 h / 100 °C 3.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere 4.1: 1,4-diaza-bicyclo[2.2.2]octane / tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere 5.1: chloroformic acid ethyl ester; triethylamine / acetone / -20 °C / Inert atmosphere 5.2: 2 h / -20 °C 5.3: 0 °C 6.1: chloroform; ethanol / 0.75 h / 60 - 63 °C 7.1: ammonia / water / 5 h / 80 °C 7.2: 0 °C / pH 1 View Scheme
Multi-step reaction with 7 steps 1.1: di-n-propylamine / 16 h / 15 - 55 °C 2.1: hydrogen bromide / water / 72 h / 100 °C 3.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere 4.1: 1,4-diaza-bicyclo[2.2.2]octane / tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere 5.1: chloroformic acid ethyl ester; triethylamine / acetone / -20 °C / Inert atmosphere 5.2: 2 h / -20 °C 5.3: 0 °C 6.1: acetone / water / 80 °C 7.1: ammonia / water / 5 h / 80 °C 7.2: 0 °C / pH 1 View Scheme

2-isobutyl-propane-1,1,3,3-tetracarboxylic acid tetraethyl ester (102710-09-8) → (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid (181289-33-8)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: hydrogen bromide / water / 72 h / 100 °C 2.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere 3.1: ammonia / water; tert-butyl methyl ether / 0 - 20 °C 3.2: pH 2 4.1: acetone / water / 80 °C 5.1: ammonia / water / 5 h / 80 °C 5.2: 0 °C / pH 1 View Scheme
Multi-step reaction with 5 steps 1.1: hydrogen bromide / water / 72 h / 100 °C 2.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere 3.1: ammonia / water; tert-butyl methyl ether / 0 - 20 °C 3.2: pH 2 4.1: chloroform; ethanol / 0.75 h / 60 - 63 °C 5.1: ammonia / water / 5 h / 80 °C 5.2: 0 °C / pH 1 View Scheme
Multi-step reaction with 6 steps 1.1: hydrogen bromide / water / 72 h / 100 °C 2.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere 3.1: 1,4-diaza-bicyclo[2.2.2]octane / tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere 4.1: chloroformic acid ethyl ester; triethylamine / acetone / -20 °C / Inert atmosphere 4.2: 2 h / -20 °C 4.3: 0 °C 5.1: chloroform; ethanol / 0.75 h / 60 - 63 °C 6.1: ammonia / water / 5 h / 80 °C 6.2: 0 °C / pH 1 View Scheme
Multi-step reaction with 6 steps 1.1: hydrogen bromide / water / 72 h / 100 °C 2.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere 3.1: 1,4-diaza-bicyclo[2.2.2]octane / tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere 4.1: chloroformic acid ethyl ester; triethylamine / acetone / -20 °C / Inert atmosphere 4.2: 2 h / -20 °C 4.3: 0 °C 5.1: acetone / water / 80 °C 6.1: ammonia / water / 5 h / 80 °C 6.2: 0 °C / pH 1 View Scheme

(1'SR,3 SR)-1-(1'-napthyl)ethyl-3-(carboxylomethyl)-5-methylhexanoate (1385049-46-6) → (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid (181289-33-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: chloroformic acid ethyl ester; triethylamine / acetone / -20 °C / Inert atmosphere 1.2: 2 h / -20 °C 1.3: 0 °C 2.1: acetone / water / 80 °C 3.1: ammonia / water / 5 h / 80 °C 3.2: 0 °C / pH 1 View Scheme
Multi-step reaction with 3 steps 1.1: chloroformic acid ethyl ester; triethylamine / acetone / -20 °C / Inert atmosphere 1.2: 2 h / -20 °C 1.3: 0 °C 2.1: chloroform; ethanol / 0.75 h / 60 - 63 °C 3.1: ammonia / water / 5 h / 80 °C 3.2: 0 °C / pH 1 View Scheme

R-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid quinine salt → (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid (181289-33-8)

Conditions	Yield
Stage #1: R-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid quinine salt With ammonia In water at 80℃; for 5h; Stage #2: With hydrogenchloride In water at 0℃; pH=1;

1,5-diallyl 3-isobutylpentanedioate (1403953-90-1) → (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid (181289-33-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: immobilized lipase B from Candida antartica; sodium hydroxide / aq. phosphate buffer / 15.6 h / 25 °C / pH 7 / Enzymatic reaction 2.1: magnesium nitride / methanol / 16 h / 20 - 80 °C 2.2: pH 3 - 4 View Scheme

Upstream product

• 916982-10-0 3-isobutylglutarimide 
• 145328-03-6 1,5-dimethy 3-isobutylpentanedioate 
• 868-52-0 2?cyano?5?methylhex?2?enoic acid methyl ester 
• 1403953-90-1 1,5-diallyl 3-isobutylpentanedioate 
• 1403953-91-2 (3S)-3-(2-(allyloxy)-2-oxoethyl)-5-methylhexanoic acid 
• 1385049-51-3 R-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid 1-phenylpropylamine salt 
• 1385049-46-6 (1'SR,3 SR)-1-(1'-napthyl)ethyl-3-(carboxylomethyl)-5-methylhexanoate 
• 102710-09-8 2-isobutyl-propane-1,1,3,3-tetracarboxylic acid tetraethyl ester 
• 51615-30-6 diethyl 2-(3-methylbutylidene)malonate 
• 185815-59-2 3-isobutylglutaric anhydride 
• 590-86-3 isovaleraldehyde 
• 181289-34-9 (S)?3?carbamoylmethyl?5?methylhexanoic acid 
• 75143-89-4 5-methyl-3-carboxymethylhexanoic acid 
• 181289-15-6 (±)?3?(carbamoylmethyl)?5?methylhexanoic acid 

Downstream Products

• 1237492-12-4 C₁₅H₂₀N₂O₅ 
• 75143-89-4 5-methyl-3-carboxymethylhexanoic acid 
• 148553-50-8 pregabilin 
• 61312-87-6 4-(2-methylpropyl)pyrrolidin-2-one 
• 181289-23-6 (S)-4-isobutyl-pyrrolidin-2-one 
• 1136478-30-2 3-(aminomethyl)-5-methylhex-5-enoic acid 
• 128013-69-4 (R,S)-3-iso-butyl-4-aminobutyric acid 
• 216576-74-8 3-(aminomethyl)-5-methylhex-4-enoic acid 

Relevant articles and documents

Synthesis and characterization of impurities of an anticonvulsant drug, Pregabalin

During the process development of Pregabalin 1, a known anticonvulsant drug, six potential impurities were identified in the final crude material ranging from 0.01 to 0.15% by LCMS. All six impurities were subsequently synthesized and characterized by IR, MS and NMR spectral data. Four of the six related substances are known as 4-isobutylpyrrolidin-2-one 6, 3-isobutylglutaric acid 2, (R)-(-)-3-carbamoylmethyl-5-methylhexanoic acid 5 and (R)-(-)-3-aminomethyl-5-methylhexanoic acid 8, whilst (S)-3-aminomethyl-5- methylhexanoic acid isobutyl ester 9 and (S)-3-aminomethyl-5-methylhexanoic acid isopropyl ester 10 are new compounds reported for the first time in our process. The present work describes the formation, synthesis and characterization of these impurities. ARKAT USA, Inc.

Method for preparing pregabalin intermediate

The invention discloses a method for preparing a pregabalin intermediate, namely, R-3-isobutyl glutaric acid monoamide. The method comprises the following steps: (1) adding 3-isobutyl glutaric acid monoamide into a system of chloroform and an alcohol solv

AN IMPROVED PROCESS FOR THE PREPARATION OF PREGABALIN

The present invention relates to an improved process for the preparation of 3-isobutyl glutaric acid compound of formula-1 which is used as the key intermediate in the preparation of Pregabalin compound of formula-A. The present invention also relates to an improved process for the preparation of (S)-3-(aminomethyl)-5-methylhexanoic acid compound of formula-A.