Production Method 1

4412-10-6

938-79-4

Reaction Conditions

1.1 Reagents: Cesium carbonate ,  Hydrogen Catalysts: [(1,2,5,6-η)-1,5-Cyclooctadiene][(1S)-7′-(diphenylphosphino-κP)-2,2′,3,3′-tetrah… Solvents: 1-Butanol ;  6 h, 0.3 MPa, 65 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  < pH 3

Reference

Spiro-phosphine-carboxylic acid iridium complex and preparation method and application thereof

, China, , ,

Production Method 2

20432-26-2

938-79-4

Reaction Conditions

1.1 Reagents: Cesium carbonate ,  Hydrogen Catalysts: Iridium(1+), [(1S)-7′-[bis[3,5-bis(1,1-dimethylethyl)phenyl]phosphino-κP]-2,2′,3… Solvents: Methanol ;  12 h, 6 atm, 45 °C

Reference

Enantioselective Hydrogenation of α-Substituted Acrylic Acids Catalyzed by Iridium Complexes with Chiral Spiro Aminophosphine Ligands

Zhu, Shou-Fei; Yu, Yan-Bo; Li, Shen; Wang, Li-Xin; Zhou, Qi-Lin, Angewandte Chemie, 2012, 51(35), 8872-8875

Production Method 3

85549-10-6

938-79-4

Reaction Conditions

1.1 Reagents: Sodium periodate Catalysts: Ruthenium trichloride Solvents: Carbon tetrachloride ,  Acetonitrile ,  Water ;  overnight, rt

Reference

Design of Hemilabile N,N,N-Ligands in Copper-Catalyzed Enantioconvergent Radical Cross-Coupling of Benzyl/Propargyl Halides with Alkenylboronate Esters

Wang, Peng-Fei; Yu, Jiao; Guo, Kai-Xin; Jiang, Sheng-Peng; Chen, Ji-Jun; et al, Journal of the American Chemical Society, 2022, 144(14), 6442-6452

Production Method 4

938-79-4

Reaction Conditions

1.1 Reagents: Butyllithium Catalysts: (αR)-N-(2,2-Dimethylpropyl)-α-phenyl-1-piperidineethanamine Solvents: Tetrahydrofuran ,  Hexane

Reference

Enantioselective α-alkylation of phenylacetic acid using a chiral bidentate lithium amide as a chiral auxiliary

Matsuo, Jun-Ichi; Koga, Kenji, Chemical & Pharmaceutical Bulletin, 1997, 45(12), 2122-2124

Production Method 5

1268614-23-8

938-79-4

Reaction Conditions

1.1 Reagents: Water ,  (2S)-2-Phenyl-1-[3-(2-pyridinyl)-1H-pyrazol-1-yl]-1-butanone Catalysts: Triacylglycerol lipase Solvents: tert-Butyl methyl ether ;  2 h, 45 °C

Reference

Kinetic resolution of (R,S)-pyrazolides containing substituents in the leaving pyrazole for increased lipase enantioselectivity

Wang, Pei-Yun; Wu, Chia-Hui; Ciou, Jyun-Fen; Wu, An-Chi; Tsai, Shau-Wei, Journal of Molecular Catalysis B: Enzymatic, 2010, 66(1-2), 113-119

Production Method 6

90-27-7

938-79-4

Reaction Conditions

1.1 Reagents: (1S,2S)-1-Amino-2,3-dihydro-1H-benz[f]inden-2-ol Solvents: Ethanol ,  Water ;  reflux; reflux → 26 °C; 12 h, 26 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  rt

Reference

Synthesis, absolute configuration, and application of enantiopure trans-1-aminobenz[f]indan-2-ol

Kobayashi, Yuka; Kinbara, Kazushi; Sato, Masaaki; Saigo, Kazuhiko, Chirality, 2005, 17(2), 108-112

Production Method 7

796849-43-9

938-79-4

938-79-4

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Water ;  rt

Reference

Rational Design of CH/π Interaction Sites in a Basic Resolving Agent

Kobayashi, Yuka; Kurasawa, Toshie; Kinbara, Kazushi; Saigo, Kazuhiko, Journal of Organic Chemistry, 2004, 69(22), 7436-7441

Production Method 8

938-79-4

Reaction Conditions

Reference

Preparation of prostaglandin analogs for methods, systems, and compositions for promoting bone growth

, World Intellectual Property Organization, , ,

Production Method 9

938-79-4

Reaction Conditions

Reference

Synthesis of chiral disulfides: potential reagents for enantioselective sulfurization

Mukhlall, Joshua A.; Noll, Bruce C.; Hersh, William H., Journal of Sulfur Chemistry, 2011, 32(3), 199-212

Production Method 10

938-79-4

Reaction Conditions

Reference

Preparation of 1-substituted 2-oxabicyclo[3.3.0]octanes and optical resolution via them

, Japan, , ,

Production Method 11

20432-26-2

938-79-4

Reaction Conditions

1.1 Reagents: Triethylamine ,  Hydrogen Catalysts: Iridium(1+), [(4S)-2-[(5R)-6-[bis(2-methylphenyl)phosphino-κP]spiro[4.4]nona-1,6… Solvents: Methanol ;  20 h, 30 atm, 50 °C

Reference

Highly enantioselective hydrogenation of α-aryl-β-substituted acrylic acids catalyzed by Ir-SpinPHOX

Zhang, Yi; Han, Zhaobin; Li, Fuying; Ding, Kuiling; Zhang, Ao, Chemical Communications (Cambridge, 2010, 46(1), 156-158

Production Method 12

4412-10-6

938-79-4

Reaction Conditions

1.1 Reagents: Cesium carbonate ,  Hydrogen Catalysts: [(1,2,5,6-η)-1,5-Cyclooctadiene][(1S)-7′-(diphenylphosphino-κP)-2,2′,3,3′-tetrah… Solvents: 1-Butanol ;  6 h, 3 atm, 65 °C

Reference

Neutral iridium catalysts with chiral phosphine-carboxy ligands for asymmetric hydrogenation of unsaturated carboxylic acids

Yang, Shuang; Che, Wen; Wu, Hui-Ling; Zhu, Shou-Fei; Zhou, Qi-Lin, Chemical Science, 2017, 8(3), 1977-1980

Production Method 13

112211-96-8

938-79-4

Reaction Conditions

1.1 Reagents: Iodoethane

Reference

Asymmetric synthesis using chiral bases. Enantioselective α-alkylation of carboxylic acids

Ando, Akira; Shioiri, Takayuki, Journal of the Chemical Society, 1987, (9), 656-8

Production Method 14

1187670-11-6

938-79-4

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Tetrahydrofuran ;  24 h, rt

Reference

An effective kinetic resolution of racemic α-arylpropanoic acids, α-arylbutanoic acids, and β-substituted-α-arylpropanoic acids with bis(9-phenanthryl)methanol as a new achiral nucleophile in the asymmetric esterification using carboxylic anhydrides and the acyl-transfer catalyst

Nakata, Kenya; Onda, Yu-suke; Ono, Keisuke; Shiina, Isamu, Tetrahedron Letters, 2010, 51(43), 5666-5669

Production Method 15

2114-36-5

938-79-4

Reaction Conditions

1.1 Reagents: Tetraethylammonium iodide Catalysts: Silver ,  [[2,2′-[(1R,2R)-1,2-Cyclohexanediylbis[(nitrilo-κN)methylidyne]]bis[4,6-bis(1,1-… Solvents: Acetonitrile ;  1 atm, rt

Reference

Entrapment of a chiral cobalt complex within silver: a novel heterogeneous catalyst for asymmetric carboxylation of benzyl bromides with CO2

Yang, Heng-Pan; Yue, Ying-Na; Sun, Qi-Long; Feng, Qiu; Wang, Huan; et al, Chemical Communications (Cambridge, 2015, 51(61), 12216-12219

Production Method 16

769-68-6

938-79-4

Reaction Conditions

1.1 Reagents: Tripotassium phosphate Catalysts: Nitrilase [91-arginine,108-serine,139-phenylalanine,163-tryptophan,166-leucine,2… Solvents: Methanol ,  Water ;  overnight, pH 8, 30 °C

Reference

Engineering of Bradyrhizobium japonicum nitrilase variants with improved performance characteristics, and use for biocatalytic production of fine chemicals

, World Intellectual Property Organization, , ,

Production Method 17

72289-61-3

938-79-4

Reaction Conditions

1.1 Catalysts: Triacylglycerol lipase Solvents: Acetonitrile ,  Water ;  0.5 min, pH 8.0, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified

Reference

Directed Evolution of an Enantioselective Lipase with Broad Substrate Scope for Hydrolysis of α-Substituted Esters

Engstroem, Karin; Nyhlen, Jonas; Sandstroem, Anders G.; Baeckvall, Jan-E., Journal of the American Chemical Society, 2010, 132(20), 7038-7042

Production Method 18

1636-25-5

938-79-4

Reaction Conditions

1.1 Catalysts: Arylmalonate decarboxylase Solvents: Water ;  pH 8.5, 25 °C
1.2 Reagents: Hydrochloric acid Solvents: Water

Reference

Effect of conformation of the substrate on enzymic decarboxylation of α-arylmalonic acid

Miyamoto, Kenji; Ohta, Hiromichi; Osamura, Yoshihiro, Bioorganic & Medicinal Chemistry, 1994, 2(6), 469-75

Production Method 19

938-79-4

Reaction Conditions

Reference

Catalytic Asymmetric Hiyama Cross-Couplings of Racemic α-Bromo Esters

Dai, Xing; Strotman, Neil A.; Fu, Gregory C., Journal of the American Chemical Society, 2008, 130(11), 3302-3303

Production Method 20

938-79-4

Reaction Conditions

Reference

Chiral discrimination of 2-arylalkanoic acids by (1S,2R)-1-aminoindan-2-ol through the formation of a consistent columnar supramolecular hydrogen-bond network

Kinbara, Kazushi; Kobayashi, Yuka; Saigo, Kazuhiko, Perkin 2, 2000, (1), 111-119

(2R)-2-phenylbutanoic acid Raw materials

• (2E)-2-phenylbut-2-enoic acid
• (1-Bromopropyl)benzene
• (2R)-2-Phenyl-1-[3-(2-pyridinyl)-1H-pyrazol-1-yl]-1-butanone
• Benzene, [(1S)-1-ethyl-2-propenyl]-
• 1H-Benz[f]inden-2-ol,1-amino-2,3-dihydro-, (1R,2S)-
• 2-Phenylbutyronitrile
• (E)-2-Phenylbut-2-enoic acid
• Benzenemethanamine, α-[(1,1-dimethylethoxy)methyl]-N-(1-methylethyl)-, lithium salt, (R)- (9CI)
• Benzeneacetic acid, α-ethyl-, 4-nitrophenyl ester
• (2R)-2-phenylbutanoic acid
• 2-Phenylbutyric acid
• Propanedioic acid,2-ethyl-2-phenyl-

(2R)-2-phenylbutanoic acid Preparation Products

• (2R)-2-phenylbutanoic acid (938-79-4)

• 1. Fatty acid eutectic mixtures and derivatives from non-edible animal fat as phase change materials?
  Pau Gallart-Sirvent,Marc Martín,Gemma Villorbina,Mercè Balcells,Aran Solé,Luisa F. Cabeza,Ramon Canela-Garayoa RSC Adv., 2017,7, 24133-24139
• 2. Fe/S-Catalyzed synthesis of 2-benzoylbenzoxazoles and 2-quinolylbenzoxazoles via redox condensation of o-nitrophenols with acetophenones and methylquinolines?
  Thi Thu Tram Nguyen,Thanh Binh Nguyen Org. Biomol. Chem., 2021,19, 6015-6020
• 3. Excimer and exciplex formation in a pair of bright phosphorescent isomers constructed from Cu3(pyrazolate)3 and Cu3I3 coordination luminophores?
  Shun-Ze Zhan,Mian Li,Xiao-Ping Zhou,Dan Li,Seik Weng Ng RSC Adv., 2011,1, 1457-1459
• 4. Emerging enantiomeric resolution materials with homochiral nano-fabrications
  Ji-Ping Wei Nanoscale, 2015,7, 11815-11832
• 5. Fe3O4 nanoparticle chains with N-doped carbon coating: magnetotactic bacteria assisted synthesis and high-rate lithium storage?
  Dan Yang,Yanping Zhou,Xianhong Rui,Jixin Zhu,Ziyang Lu,Eileen Fong,Qingyu Yan RSC Adv., 2013,3, 14960-14962

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Phenylpropanes

• 3508-94-9(3-Methyl-2-phenylbutanoic Acid)
• 635-51-8(2-phenylbutanedioic acid)
• 4286-15-1((2S)-2-phenylbutanoic acid)
• 15935-54-3(Ibuprofen Carboxylic Acid(Mixture of Diastereomers))
• 108789-32-8(Benzeneacetic acid, a-ethyl-4-(2-methylpropyl)-,labeled with tritium (9CI))
• 4036-30-0((S)-(+)-Phenylsuccinic acid)
• 149646-92-4((S)-Butibufen)
• 46292-93-7((R)-Phenylsuccinic Acid)
• 90-27-7(2-Phenylbutyric acid)
• 110319-84-1(3-methyl-2-4-(2-methylpropyl)phenylbutanoic acid)