Production Method 1

37088-66-7

82769-76-4

Reaction Conditions

1.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; 2 h, rt
1.2 Reagents: Sodium sulfate Solvents: Water ;  rt

Reference

Short enantioselective routes to (S)-Dapoxetine

Rapolu, Rajesh Kumar; et al, Chemistry & Biology Interface, 2013, 3(1), 50-60

Production Method 2

718611-17-7

82769-76-4

Reaction Conditions

1.1 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ;  30 min, 0 °C; 0 °C → rt; 1.5 h, rt
1.2 Reagents: Triethylamine Solvents: Methanol

Reference

An efficient formal synthesis of (S)-dapoxetine from enantiopure 3-hydroxy azetidin-2-one

Chincholkar, Pinak M.; et al, Tetrahedron, 2009, 65(12), 2605-2609

Production Method 3

82769-76-4

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Iodine Solvents: Tetrahydrofuran ,  Water ;  50 °C

Reference

Iodine mediated deprotection of N-tert-butanesulfinyl amines: a functional group compatible method

Chen, Wen; et al, Chemical Communications (Cambridge, 2014, 50(47), 6259-6262

Production Method 4

869468-32-6

82769-76-4

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethyl acetate

Reference

Highly Efficient, Enantioselective Syntheses of (S)-(+)- and (R)-(-)-Dapoxetine Starting with 3-Phenyl-1-propanol

Kang, Soyeong; et al, Journal of Organic Chemistry, 2010, 75(1), 237-240

Production Method 5

869468-32-6

82769-76-4

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  16 h, rt

Reference

Syntheses of a Flobufen Metabolite and Dapoxetine Based on Enantioselective Allylation of Aromatic Aldehydes

Hessler, Filip; et al, European Journal of Organic Chemistry, 2014, 2014(12), 2543-2548

Production Method 6

126568-44-3

82769-76-4

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Water ;  overnight, reflux
1.2 Reagents: Sodium hydroxide Solvents: Water ;  basified
1.3 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; overnight, reflux
1.4 Reagents: Sodium hydroxide Solvents: Water

Reference

Kinetic and NMR spectroscopic studies of chiral mixed sodium/lithium amides used for the deprotonation of cyclohexene oxide

Sott, Richard; et al, Chemistry - A European Journal, 2005, 11(16), 4785-4792

Production Method 7

40856-44-8

82769-76-4

Reaction Conditions

1.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  0 °C; 0 °C → reflux; 5 h, reflux; reflux → 0 °C
1.2 Reagents: Sodium hydroxide Solvents: Water ;  0 °C

Reference

Synthesis of (S)-dapoxetine by biomethod

Zhang, De-rong; et al, Shengwu Jiagong Guocheng, 2010, 8(2), 13-17

Production Method 8

936499-93-3

82769-76-4

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Water ;  basified, rt

Reference

Preparation of enantiomerically pure (R)- and (S)-3-amino-3-phenyl-1-propanol via resolution with immobilized penicillin G acylase

Fadnavis, Nitin W.; et al, Tetrahedron: Asymmetry, 2006, 17(2), 240-244

Production Method 9

82769-76-4

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Water ;  23 h, 50 °C
1.2 Reagents: Ammonium hydroxide ;  basified

Reference

Lipase-catalyzed resolution of chiral 1,3-amino alcohols: application in the asymmetric synthesis of (S)-dapoxetine

Torre, Oliver; et al, Tetrahedron: Asymmetry, 2006, 17(5), 860-866

Production Method 10

82769-76-4

Reaction Conditions

1.1 Reagents: Tributylstannane Catalysts: Azobisisobutyronitrile Solvents: Toluene ;  rt; rt → reflux; 6 h, reflux
1.2 Reagents: Trifluoroacetic acid Solvents: Tetrahydrofuran ;  10 °C; 5 h, rt
1.3 Reagents: Sodium hydroxide Solvents: Water ;  0 °C

Reference

A stereoselective synthesis of (S)-dapoxetine starting from trans-cinnamyl alcohol

Venkatesan, K.; et al, ARKIVOC (Gainesville, 2008, (16), 302-310

Production Method 11

3082-69-7

82769-76-4

Reaction Conditions

1.1 Reagents: Lithium aluminum hydride

Reference

High asymmetric induction in the 1,3-dipolar cycloaddition of (R)-(+)-p-tolyl vinyl sulfoxide with acyclic nitrones

Koizumi, Toru; et al, Journal of Organic Chemistry, 1982, 47(20), 4004-5

Production Method 12

126568-44-3

82769-76-4

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Methanol ,  Water ;  rt; 1 h, rt; 5 h, rt → reflux
1.2 Reagents: Triethylamine Solvents: Ethanol ;  15 min
2.1 Reagents: Sodium triacetoxyborohydride Solvents: Tetrahydrofuran ;  10 min, 0 °C
2.2 Reagents: Boron trifluoride etherate ;  0 °C; 5 h, 0 °C
2.3 Reagents: Methanol ;  0 °C

Reference

Synthesis of Dapoxetine

Ning, Yan-shi; et al, Huaxue Shiji, 2015, 37(2), 185-188

Production Method 13

82769-76-4

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water ;  18 h, reflux

Reference

Scope and computational insights into enantioselective C-H amination through silver-catalyzed nitrene transfer

Schroeder, Emily Z.; et al, ChemRxiv, 2023, 1, 1-10

Production Method 14

1067647-06-6

82769-76-4

Reaction Conditions

1.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  0 °C → rt; rt
1.2 Reagents: Sodium sulfate Solvents: Water ;  1 h, rt
2.1 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ;  30 min, 0 °C; 0 °C → rt; 1.5 h, rt
2.2 Reagents: Triethylamine Solvents: Methanol

Reference

An efficient formal synthesis of (S)-dapoxetine from enantiopure 3-hydroxy azetidin-2-one

Chincholkar, Pinak M.; et al, Tetrahedron, 2009, 65(12), 2605-2609

(3S)-3-amino-3-phenylpropan-1-ol Raw materials

• (3S)-3-amino-3-phenylpropanoic acid
• (S)-Boc-3-Amino-3-Phenylpropan-1-Ol
• Carbamic acid, (2-cyano-1-phenylethyl)-, 1,1-dimethylethyl ester, (S)-
• (3s)-3-amino-3-phenylpropan-1-ol;hydrochloride
• (S)-2-oxo-4-phenyl-azetidine-1-carboxylic acid tert-butyl ester
• (S)-Cbz-3-Amino-3-phenylpropan-1-ol
• methyl (3S)-3-amino-3-phenylpropanoate
• (βS)-β-Aminobenzenepropanoic Acid Ethyl Ester

(3S)-3-amino-3-phenylpropan-1-ol Preparation Products

• (3S)-3-amino-3-phenylpropan-1-ol (82769-76-4)

• 1. Fate of Sb(v) and Sb(iii) species along a gradient of pH and oxygen concentration in the Carnoulès mine waters (Southern France)
  Eléonore Resongles,Corinne Casiot,Fran?oise Elbaz-Poulichet,Rémi Freydier,Odile Bruneel,Christine Piot,Sophie Delpoux,Aurélie Volant,Angélique Desoeuvre Environ. Sci.: Processes Impacts, 2013,15, 1536-1544
• 2. 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
• 3. Emerging investigator series: first-principles and thermodynamics comparison of compositionally-tuned delafossites: cation release from the (001) surface of complex metal oxides?
  Joseph W. Bennett,Diamond T. Jones,Blake G. Hudson,Joshua Melendez-Rivera,Robert J. Hamers,Sara E. Mason Environ. Sci.: Nano, 2020,7, 1642-1651
• 4. 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
• 5. Fast-Track to Research Data Management in Experimental Material Science-Setting the Ground for Research Group Level Materials Digitalization.
  LarsBanko,AlfredLudwig

• Solvents and Organic Chemicals Organic Compounds Organic nitrogen compounds Organonitrogen compounds Aralkylamines
• Solvents and Organic Chemicals Organic Compounds Organic nitrogen compounds Organonitrogen compounds Amines Aralkylamines
• Solvents and Organic Chemicals Organic Compounds Alcohol/Ether

Compound CAS No. 82769-76-4: (3S)-3-Amino-3-Phenylpropan-1-Ol

(3S)-3-Amino-3-Phenylpropan-1-Ol, also known by its CAS number 82769-76-4, is a chiral organic compound with significant applications in various fields, including pharmaceuticals, biotechnology, and organic synthesis. This compound is characterized by its unique structure, which combines an amino group (-NH?) and a phenyl group (-C?H?) attached to a chiral carbon atom in a propanol backbone. The (S)-configuration at the chiral center imparts specific stereochemical properties, making it highly valuable in asymmetric synthesis and enantioselective reactions.

The molecular formula of (3S)-3-Amino-3-Phenylpropan-1-Ol is C?H??NO, with a molecular weight of approximately 135.18 g/mol. Its structure consists of a central carbon atom bonded to an amino group, a phenyl group, a hydroxyl group (-OH), and a methyl group (-CH?). The presence of the hydroxyl group makes it an alcohol, while the amino group contributes to its ability to form hydrogen bonds and participate in various chemical reactions. The phenyl group introduces aromaticity and enhances the compound's stability and reactivity in certain conditions.

Recent studies have highlighted the importance of (3S)-3-Amino-3-Phenylpropan-1-Ol in the development of novel therapeutic agents. For instance, researchers have explored its role as a building block in the synthesis of bioactive molecules, including peptide analogs and small-molecule inhibitors. Its chiral nature makes it particularly useful in asymmetric catalysis, where it can serve as a substrate or a catalyst for enantioselective reactions. This has led to its application in the production of enantiopure compounds, which are critical in drug discovery and development.

In addition to its role in pharmaceuticals, (3S)-3-Amino-3-Phenylpropan-1-Ol has found applications in the field of materials science. Its ability to form stable complexes with metal ions has been leveraged in the synthesis of coordination polymers and metalloorganic frameworks (MOFs). These materials exhibit unique properties, such as high surface area and tunable pore sizes, making them ideal for gas storage, catalysis, and sensing applications.

The synthesis of (3S)-3-Amino-3-Phenylpropan-1-Ol typically involves multi-step processes that require precise control over stereochemistry. Common methods include asymmetric reduction of ketones using chiral catalysts or enzymatic resolution of racemic mixtures. Recent advancements in catalytic asymmetric synthesis have enabled more efficient and scalable production methods for this compound, further enhancing its utility in industrial applications.

From an environmental standpoint, researchers have also investigated the biodegradability and eco-friendly synthesis routes for (3S)-3-Amino-3-Phenylpropan-1-Ol. Green chemistry approaches, such as using renewable feedstocks and minimizing waste generation, have been employed to develop sustainable methods for its production. These efforts align with global initiatives to reduce environmental impact while maintaining high standards of product quality.

In conclusion, (3S)-3-Amino-3-Phenylpropan-1-Ol (CAS No. 82769-76-) is a versatile compound with wide-ranging applications across multiple disciplines. Its unique structure, chiral properties, and reactivity make it an invaluable tool in chemical research and industry. As advancements continue to be made in synthetic methodologies and application development, this compound is expected to play an even more significant role in shaping future innovations.

• 936499-92-2((3r)-3-amino-3-phenyl-1-propanol Hydrochloride (1:1))
• 1071436-36-6((R)-3-Amino-3-(4-methylphenyl)propan-1-ol)
• 170564-98-4((R)-3-Amino-3-phenylpropan-1-ol)
• 68208-22-0(3-m-tolyl-dl-β-alaninol)
• 936499-93-3((3s)-3-amino-3-phenylpropan-1-ol;hydrochloride)
• 1213645-36-3((3S)-3-amino-3-(4-methylphenyl)propan-1-ol)
• 14593-04-5(3-Amino-3-phenyl-1-propanol)
• 683220-57-7(3-amino-3-(4-ethylphenyl)propan-1-ol)
• 1212834-96-2((S)-3-M-Tolyl-β-alaninol)
• 68208-23-1(3-Amino-3-(4-methylphenyl)propan-1-ol)