522644-10-6

Usage

Uses

Used in Pharmaceutical Research and Development:
(1S,2R)-2-AMINO-CYCLOOCTANECARBOXYLIC ACID HYDROCHLORIDE is used as a building block for the synthesis of various drugs and bioactive compounds due to its unique chiral structure and potential medicinal properties.
Used in Organic Chemistry:
(1S,2R)-2-AMINO-CYCLOOCTANECARBOXYLIC ACID HYDROCHLORIDE is utilized in the field of organic chemistry for its potential applications in creating novel molecules and advancing chemical reactions.
Used in Drug Discovery:
(1S,2R)-2-AMINO-CYCLOOCTANECARBOXYLIC ACID HYDROCHLORIDE serves as a valuable tool in drug discovery, aiding researchers in the development of new therapeutic agents and enhancing the understanding of molecular interactions.

InChI:InChI=1/C9H17NO2.ClH/c10-8-6-4-2-1-3-5-7(8)9(11)12;/h7-8H,1-6,10H2,(H,11,12);1H/t7-,8+;/m0./s1

Upstream product

• 3806-59-5 1,3-cyclooctadiene 
• 24571-99-1 (Z)-9-azabicyclo[6.2.0]dec-6-en-10-one 
• 19297-13-3 ethyl cis-2-hydroxy-1-cyclooctane carboxylate 
• 772330-11-7 ethyl trans-2-aminocyclooctanecarboxylate 
• 772330-11-7 (1R,2R)-ethyl 2-aminocyclooctanecarboxylate 
• 522644-04-8 (1R,2S)-2-Amino-cyclooctanecarboxylic acid 
• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 4017-56-5 ethyl 2-oxocyclooctane-1-carboxylate 
• 193065-63-3 (1R,2S)-(+)-ethyl 2-hydroxycyclooctanecarboxylate 

Relevant academic research and scientific papers

Lipase-catalyzed enantioselective ring opening of unactivated alicyclic-fused beta-lactams in an organic solvent.

[reaction: see text] A highly efficient and very simple method was developed for the synthesis of enantiopure beta-amino acids (e.g. cispentacin) and beta-lactams through the enzyme-catalyzed enantioselective ring opening of unactivated alicyclic beta-lac

Efficient enzymatic routes for the synthesis of new eight-membered cyclic β-amino acid and β-lactam enantiomers

Efficient enzymatic resolutions are reported for the preparation of new eight-membered ring-fused enantiomeric β-amino acids [(1R, 2S)-9 and (1S, 2R)-9] and β-lactams [(1S, 8R)-3, (1R, 8S)-3 (1S, 8R)-4 and (1R, 8S)-7], through asymmetric acylation of (±)-4 (E > 100) or enantioselective hydrolysis (E > 200) of the corresponding inactivated (±)-3 or activated (±)-4 β-lactams, catalyzed by PSIM or CAL-B in an organic solvent. CAL-B-catalyzed ring cleavage of (±)-6 (E > 200) resulted in the unreacted (1S, 8R)-6, potential intermediate for the synthesis of enantiomeric anatoxin-a. The best strategies, in view of E, reaction rate and product yields, which underline the importance of substrate engineering, are highlighted.

Synthesis of alicyclic trans-β-amino acids from cis-β- hydroxycycloalkane-carboxylates

A simple and efficient method is described for the preparation of both racemic and enantiopure trans-β-amino acids with a cycloheptane or cyclooctane skeleton, starting from racemic and enantiopure ethyl cis-2-hydroxycarboxylates. Georg Thieme Verlag Stut

Preparation of (1R,8S)- and (1S,8R)-9-azabicyclo[6.2.0]dec-4-en-10-one: Potential starting compounds for the synthesis of anatoxin-a

9-Azabicyclo[6.2.0]-dec-4-en-10-one (±)-2, obtained from cyclooctadiene by addition of chlorosulfonyl isocyanate, was N-hydroxymethylated to (±)-3 and then resolved by lipase-catalysed asymmetric acylation of the primary OH group at the (S)-stereogenic centre. High enantioselectivity (E = 94) was observed when lipase PS and vinyl butyrate were used in di-iso-propyl ether at -15°C, resulting in the enantiomerically enriched ester 3a and alcohol 3b (e.e. ≥92%). Treatment of 3a and 3b with NH4OH/MeOH afforded the corresponding β-lactams (1R,8S)-2a and (1S,8R)-2b (e.e. ≥93%), potential starting compounds in anatoxin-a synthesis. The ring opening of lactams (±)-2, (±)-7, 3a and 3b, followed by reduction, resulted in racemic 4-6 and 8 and enantiomeric 4a, 4b, 5a and 5b eight-membered cyclic β-amino acid derivatives.