63701-56-4

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Biochem/physiol Actions

S(?)-Baclofen hydrochloride is a less active enantiomer of baclofen.

InChI:InChI=1/C10H12ClNO2.ClH/c11-9-3-1-7(2-4-9)8(6-12)5-10(13)14;/h1-4,8H,5-6,12H2,(H,13,14);1H/t8-;/m1./s1

Upstream product

• 750649-51-5 (S)-(+)-3-(4-chloro-phenyl)-4-nitro-butyric acid 
• 24393-52-0 ethyl (E)-3-(4-chlorophenyl)prop-2-enoate 
• 1006386-92-0 ethyl (2S,3S)-2-bromo-3-hydroxy-3-(4-chlorophenyl)propanoate 
• 1006386-91-9 (4R,5S)-4-carbethoxy-5-(4-chlorophenyl)-1,3,2-dioxathiolane 2-oxide 
• 123632-35-9 (R)-(-)-4-(4-chlorophenyl)pyrrolidin-2-one 
• 123632-31-5 (S)-(+)-4-(4-chlorophenyl)pyrrolidin-2-one 
• 171897-46-4 (4S)-1-tert-butoxycarbonyl-4-(4-chlorophenyl)-2-pyrrolidone 
• 137310-16-8 (R)-3-(4-chlorophenyl)-glutaric acid monomethyl ester 
• 52927-44-3 dimethyl 2-(4-chlorobenzylidene)malonate 
• 360072-54-4 methyl 2-carbomethoxy-4-nitro-3-(4-chloro-phenyl)-butyrate 
• 89979-04-4 1-(4-chlorophenyl)-2-nitroethanol 
• 706-07-0 1-chloro-4-(2-nitrovinyl)benzene 
• 1186588-18-0 C₁₃H₁₆ClNO₄ 
• 137310-14-6 trimethyl 2-(4-chlorophenyl)propane-1,1,3-tricarboxylate 

Relevant academic research and scientific papers

One-Pot Synthesis of (S)-Baclofen via Aldol Condensation of Acetaldehyde with Diphenylprolinol Silyl Ether Mediated Asymmetric Michael Reaction as a Key Step

An efficient asymmetric total synthesis of (S)-baclofen was accomplished via a one-pot operation from commercially available materials using sequential reactions, such as aldol condensation of acetaldehyde, diphenylprolinol silyl ether mediated asymmetric Michael reaction of nitromethane, Kraus-Pinnick oxidation, and Raney Ni reduction. Highly enantioenriched baclofen was obtained in one pot with a good yield over four reactions.

Efficient synthesis of β-aryl-γ-lactams and their resolution with (S)-Naproxen: Preparation of (R)- and (S)-Baclofen

An efficient synthesis of enantiomerically-pure β-aryl-γ-lactams is described. The principal feature of this synthesis is the practical resolution of β-aryl-γ-lactams with (S)-Naproxen. The procedure is based on the Michael addition of nitromethane to benzylidenemalonates, which was easily obtained, followed by the reduction of the γ-nitroester in the presence of Raney nickel and the subsequent saponification/decarboxylation reaction. The utility of this methodology was highlighted by the preparation of enantiomerically-pure (R)- and (S)-Baclofen hydrochloride.

Stereoselective reaction of 2-carboxythioesters-1,3-dithiane with nitroalkenes: An organocatalytic strategy for the asymmetric addition of a glyoxylate anion equivalent

An efficient organocatalytic methodology has been developed to perform the stereoselective addition of 2-carboxythioesters-1,3-dithiane to nitroalkenes. Under mild reaction conditions γ-nitro-β-aryl-α-keto esters with up to 92% ee were obtained, realizing a formal catalytic stereoselective conjugate addition of the glyoxylate anion synthon. The reaction products are versatile starting materials for further synthetic transformations; for example, the simultaneous reduction of the nitro group and removal of the dithiane ring was accomplished, allowing the preparation of a GABAB receptor agonist baclofen.

Multisite organic-inorganic hybrid catalysts for the direct sustainable synthesis of GABAergic drugs

Multisite organic-inorganic hybrid catalysts have been prepared and applied in a new general, practical, and sustainable synthetic procedure toward industrially relevant GABA derivatives. The domino sequence is composed of seven chemical transformations which are performed in two one-pot reactions. The method produces both enantiomeric forms of the product in high enantiopurity as well as the racemate in good yields after a single column purification step. This protocol highlights major process intensification, catalyst recyclability, and low waste generation.

Rhodium-catalyzed asymmetric addition of arylboronic acids to γ-phthalimido-substituted-α,β-unsaturated carboxylic acid esters: An approach to γ-amino acids

Efficient Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to ethyl-γ-phthalimidocrotonate by using bis-sulfoxide ligand affords γ-aminobutyric acid (GABA) derivatives with high enantioselectivities (90-96% ee) under mild conditions. Optically pu

A short, chemoenzymatic route to chiral β-aryl-γ-amino acids using reductases from anaerobic bacteria

A short chemoenzymatic synthesis of β-aryl-γ-aminobutyric acids has been developed, based on a highly enantioselective biocatalytic reduction of β-aryl-β-cyano-α,β-unsaturated carboxylic acids.

An efficient synthesis of (R)- and (S)-baclofen via desymmetrization

A short and highly enantioselective synthesis of both enantiomers of GABA agonist baclofen in four steps with total yields of 32.8% [for (S)-isomer] and 35.1% [for (R)-isomer] is reported. The key step involved desymmetrization of cyclic anhydride with mo

Asymmetrie synthesis of (R)-(-)-baclofen via asymmetric dihydroxylation

A short and efficient asymmetric synthesis of (R)-(-)-baclofen, a selective GABAB agonist has been described with an overall yield of 14% and 85% ee. The Os-catalyzed Sharpless asymmetric dihydroxylation of a,β-unsaturated olefin constitutes the key step in introducing stereogenic centers into the molecule.

Diastereoselective conjugate addition of cyanide to α,β- unsaturated oxazolidinones: Enantioselective synthesis of ent-pregabalin and baclofen

Conjugate addition of cyanide to chiral α,β-unsaturated oxazolidinones catalyzed by samarium(III) isopropoxide proceeds with good diastereoselectivity. The addition products can be converted into the biologically active targets ent-pregabalin and baclofen

Synthesis of both enantiomers of baclofen using (R)- and (S)-N-phenylpantolactam as chiral auxiliaries

Esterification of racemic 4-nitro-3-(4-chlorophenyl)butanoic acid with (R)- or (S)-N-phenylpantolactam as the chiral auxiliary allowed us to obtain the (3R,3′R)- or (3S,3′S)-nitro esters with >98:2 dr after column chromatography. Hydrolysis of the resulti