Trademarks: Lyrica
Molecular Formula: C8H17NO2
CAS Registry Number: 148553-50-8
CAS Name: (S)-3-(aminomethyl)-5-methylhexanoic acid
Molecular Weight: 159.23
SMILES: CC(C)C[C@H](CN)CC(O)=O
InChI Key: AYXYPKUFHZROOJ-ZETCQYMHSA-N
InChI: InChI=1S/C8H17NO2/c1-6(2)3-7(5-9)4-8(10)11/h6-7H,3-5,9H2,1-2H3,(H,10,11)/t7-/m0/s1
Activity: Treatment of epilepsy, postherpetic neuralgia, diabetic peripheral neuropathy, fibromyalgia; Gabapentin successor; Treatment of Neuropathic Pain; Treatment of Anxiety disorder; Anticonvulsants
Status: Launched 2004
Originator: Pfizer
Many routes for synthesis of Pregabalin are reported in literature. I will report the best and competitive ones.
Racemic Pregabalin: Synthesis 1989, 12, 953-955
Pregabalin synthesis: Malonate approach, favoured by most text (WO1996040617A1; also Ref. 2)
Pregabalin synthesis: L-leucine approach (Org Process Res Dev 1997, 1(1), 26-38)
References:
1. Grote, T. M.; et. al. Method of making (S)-3-(aminomethyl)-5-methylhexanoic acid. WO1996040617A1
2. Hoekstra, M. S.; et. al. Chemical Development of CI-1008, an Enantiomerically Pure Anticonvulsant. Org Process Res Dev 1997, 1(1), 26-38.3. Silverman, R. B.; et. al. A Convenient Synthesis of 3-Alkyl-4-aminobutanoic Acids. Synthesis, 1989, 12, 953-955.
