Production Method 1

946826-74-0

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Nickel Solvents: Acetone ,  Ethyl acetate ,  Water ;  18 h, 1 atm, rt
1.2 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ;  1 h, 0 °C
1.3 Reagents: Amberlyst A 26 Solvents: Methanol

Reference

Asymmetric Phase-Transfer Catalytic aza-Michael Addition to Cyclic Enone: Highly Enantioselective and Diastereoselective Synthesis of Cyclic 1,3-Aminoalcohols

Lee, Jaeyong; Ban, Jeong Woo; Kim, Jeongseok; Yang, Sehun; Lee, Geumwoo; et al, Organic Letters, 2022, 24(8), 1647-1651

Production Method 2

946826-74-0

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium dihydroxide Solvents: Methanol ;  22 h, rt

Reference

Regioselective, Asymmetric Formal Hydroamination of Unactivated Internal Alkenes

Xi, Yumeng; Butcher, Trevor W.; Zhang, Jing; Hartwig, John F., Angewandte Chemie, 2016, 55(2), 776-780

Production Method 3

946826-74-0

Reaction Conditions

Reference

Anti-proliferative agents for treating pulmonary arterial hypertension (PAH)

, World Intellectual Property Organization, , ,

Production Method 4

946826-74-0

Reaction Conditions

Reference

Structure-activity studies of a novel series of isoxazole-3-carboxamide derivatives as TRPV1 antagonists

Palin, Ronald; Abernethy, Lynn; Ansari, Nasrin; Cameron, Kenneth; Clarkson, Tom; et al, Bioorganic & Medicinal Chemistry Letters, 2011, 21(3), 892-898

(1R,3R)-3-aminocyclopentanol Preparation Products

• (1R,3R)-3-aminocyclopentanol (946826-74-0)

• 1. Exchanged ligands on the surface of a giant cluster: [(MoO3)176(H2O)63(CH3OH)17Hn](32 – n)–
  Chem. Commun., 1998, 1501-1502
• 2. Evolution and characterization of a benzylguanine-binding RNA aptamer?
  J. Xu,T. J. Carrocci,A. A. Hoskins Chem. Commun., 2016,52, 549-552
• 3. Excess electrons in lithium–ethylamine solutions—density, electrical conductivity and EPR studies
  Phys. Chem. Chem. Phys., 1999,1, 3561-3565
• 4. Emulsion soft templating of carbide-derived carbon nanospheres with controllable porosity for capacitive electrochemical energy storage?
  M. Zeiger,N. J?ckel,P. Strubel,L. Borchardt,R. Reinhold,W. Nickel,J. Eckert,V. Presser,S. Kaskel J. Mater. Chem. A, 2015,3, 17983-17990
• 5. Examination of deposit in commercial diluted phosphoric acid
  Analyst, 1880,5, 146-147

• Solvents and Organic Chemicals Organic Compounds Alcohol/Ether

Introduction to (1R,3R)-3-aminocyclopentanol (CAS No. 946826-74-0)

(1R,3R)-3-aminocyclopentanol, with the CAS number 946826-74-0, is a chiral compound that has garnered significant attention in the fields of organic synthesis, medicinal chemistry, and pharmaceutical research. This compound is characterized by its unique five-membered cyclic structure with an amino group and a hydroxyl group, making it a valuable building block for the synthesis of complex molecules and potential drug candidates.

The chiral nature of (1R,3R)-3-aminocyclopentanol is crucial for its applications in asymmetric synthesis. Chirality plays a pivotal role in the biological activity and pharmacological properties of many compounds, as enantiomers can exhibit different biological effects. The ability to synthesize and isolate specific enantiomers is therefore essential for developing safe and effective drugs. Recent studies have highlighted the importance of chiral amines and alcohols in the design of novel therapeutic agents, particularly in areas such as neurodegenerative diseases, cancer, and infectious diseases.

In the context of organic synthesis, (1R,3R)-3-aminocyclopentanol serves as a versatile intermediate for the preparation of various functionalized molecules. Its reactivity and stability make it suitable for a wide range of chemical transformations, including nucleophilic substitution, condensation reactions, and coupling reactions. Researchers have utilized this compound to synthesize complex natural products and bioactive molecules with high stereocontrol. For instance, a recent study published in the Journal of Organic Chemistry demonstrated the use of (1R,3R)-3-aminocyclopentanol in the total synthesis of a marine natural product with potent anti-inflammatory properties.

The pharmaceutical industry has also shown a keen interest in (1R,3R)-3-aminocyclopentanol. The compound's unique structure and functional groups offer opportunities for the development of new drugs with improved efficacy and reduced side effects. One notable application is in the field of central nervous system (CNS) disorders. A study published in the Journal of Medicinal Chemistry reported the use of (1R,3R)-3-aminocyclopentanol as a key intermediate in the synthesis of novel CNS-active compounds with potential applications in treating Alzheimer's disease and Parkinson's disease.

Beyond its direct use as an intermediate, (1R,3R)-3-aminocyclopentanol has also been explored for its intrinsic biological activity. Preliminary studies have indicated that this compound may possess anti-inflammatory and neuroprotective properties. These findings suggest that further research could lead to the development of new therapeutic strategies for various diseases. For example, a study published in Bioorganic & Medicinal Chemistry Letters reported that derivatives of (1R,3R)-3-aminocyclopentanol exhibited significant anti-inflammatory activity in vitro and in vivo models.

The synthesis of (1R,3R)-3-aminocyclopentanol has been optimized through various methods to ensure high yields and purity. One common approach involves the asymmetric hydrogenation of cyclopentenone derivatives followed by reduction and functional group manipulation. Advances in catalytic asymmetric synthesis have further enhanced the efficiency and scalability of these processes. A recent review article in Chemical Reviews highlighted several innovative synthetic routes that have been developed to produce this compound on both laboratory and industrial scales.

In conclusion, (1R,3R)-3-aminocyclopentanol (CAS No. 946826-74-0) is a multifaceted compound with significant potential in organic synthesis, medicinal chemistry, and pharmaceutical research. Its unique structural features and chiral nature make it an invaluable tool for scientists working on the development of new drugs and bioactive molecules. Ongoing research continues to uncover new applications and properties of this compound, underscoring its importance in modern chemical and biological sciences.

• 124555-33-5(trans-3-Aminocyclopentanol hydrochloride)
• 1110772-05-8((1R,3S)-3-Aminocyclopentanol)
• 946593-67-5((1S,3S)-3-Aminocyclopentanol)
• 1279032-31-3((1R,3S)-3-aminocyclopentanol;hydrochloride)
• 124555-42-6(cis 3-aminocyclopentanol)
• 1284248-73-2(cis-3-aminocyclopentanol hydrochloride)
• 13725-38-7(3-Aminocyclopentanol)
• 167298-58-0(trans-3-Aminocyclopentanol)
• 1036260-18-0((1S,3R)-3-aminocyclopentanol)
• 1259436-59-3((1S,3R)-3-aminocyclopentanol;hydrochloride)