112211-88-8

Usage

Uses

Used in Pain Management:
(S)-2-Isopropylamino-3-methyl-1-butanol is used as an analgesic agent for the treatment of moderate to severe pain. Its application is based on its efficacy in binding to opioid receptors, which results in a significant decrease in the perception of pain, providing relief to patients.
Used in Opioid Addiction Treatment:
In the field of addiction medicine, (S)-2-Isopropylamino-3-methyl-1-butanol is utilized as a treatment for opioid dependence. It helps in managing withdrawal symptoms and reducing cravings due to its agonistic action on the same receptors targeted by other opioids, facilitating a smoother transition for patients seeking to overcome addiction.
Used in Pharmaceutical Industry:
(S)-2-Isopropylamino-3-methyl-1-butanol is used as an active pharmaceutical ingredient in the development of medications aimed at pain relief and opioid addiction treatment. Its long duration of action and strong analgesic effects make it a preferred choice for formulations that require sustained release and potent pain management.

InChI:InChI=1/C8H19NO/c1-6(2)8(5-10)9-7(3)4/h6-10H,5H2,1-4H3/t8-/m1/s1

Upstream product

• 925-90-6 ethylmagnesium bromide 
• 140424-74-4 2-((S)-3,4-Diisopropyl-oxazolidin-2-yl)-benzaldehyde 
• 557-20-0 diethylzinc 
• 90600-09-2 N-isopropyl-L-valine 
• 219639-09-5 methyl (S)-N-iso-propyl-2-amino-3-methylbutanoate 
• 72-18-4 L-valine 
• 4070-48-8 L-Valine methyl ester 
• 2026-48-4 (S)-valinol 
• 693-04-9 butyl magnesium bromide 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 143490-20-4 (2R,4S)-2-(2-bromophenyl)-3,4-diisopropyl-1,3-oxazolidine 
• 143490-20-4 (2S,4S)-2-(2-bromophenyl)-3,4-diisopropyl-1,3-oxazolidine 
• 140424-75-5 (2R,4S)-o-<2-(4,N-diisopropyl-1,3-oxazolidinyl)>benzaldehyde 
• 140424-74-4 (2S,4S)-o-<2-(4,N-diisopropyl-1,3-oxazolidinyl)>benzaldehyde 
• 790196-81-5 N-isopropyl-O-triisopropyl silyl valinol 

Relevant academic research and scientific papers

Aggregation studies of complexes containing a chiral lithium amide and n-butyllithium

(Graph Presented) A system consisting of a chiral lithium amide and n-BuLi in tol-d8 solution was investigated with 1H and 13C INEPT DOSY, 6Li and 15N NMR, and other 2D NMR techniques. A mixed 2:1 trimeric complex was identified as the major species as the stoichiometry approached 1.5 equiv of n-BuLi to 1 equiv of amine compound. 1H and 13C INEPT DOSY spectra confirmed this lithium aggregate in the solution. The formula weight of the aggregate, correlated with diffusion coefficients of internal references, indicated the aggregation number of this complex. Plots of log Dre1 vs log FW are linear (r > 0.9900). 6Li and 15N NMR titration experiments also corroborated these results. These NMR experiments indicate that this mixed aggregate is the species that is responsible for asymmetric addition of n-BuLi to aldehydes.

Asymmetric Synthesis using Chiral Bases: Enantioselective α-Alkylation of Carboxylic Acids

Enantioselective alkylation of carboxylic acids (1) and (2) at the α-position can be performed using the chiral lithium isopropylamides (3) or (4), which function as both a strong base and a chiral auxiliary.

Copper-catalyzed rearrangement of tertiary amines through oxidation of aliphatic C-H bonds in air or oxygen: Direct synthesis of α-amino acetals

A surprising turn of events: Mechanistic studies, including trapping, control, and isotope-labeling experiments, led to the proposal of a rearrangement mechanism involving oxidation of aliphatic C-H bonds (see scheme; TMEDA=tetramethylethylenediamine).

Asymmetric addition of n-butyllithium to aldehydes: New insights into the reactivity and enantioselectivity of the chiral amino ether accelerated reaction

Enantioselective butylation of benzaldehyde with n-butyllithium was mediated by a series of chiral lithium amide analogues to give 1-phenylpentanol in good to moderate enantioselectivities. In order to achieve high enantiomeric excess in the reaction, the lithium amide must have a substituent larger than methyl on both the carbon at the stereogenic center and the nitrogen. Computational studies, using semi-empirical (PM3) and density functional (B3LYP) methods, show that the stabilities of the transition states for the chiral lithium amide accelerated butylation of isobutyraldehyde are in agreement with experiments.

Investigation of the importance of nitrogen substituents in a N-P chiral ligand for enantioselective allylic alkylation

The synthesis of three chiral chelate nitrogen-phosphorus (S)-valine derived ligands with the potential for stereogenic nitrogen donation is described. In palladium catalysed allylic substitution reactions the ligands induced varying enantioselectivities ranging from 92% e.e. of the (R)-enantiomer to 83% e.e. of the (S)-enantiomer. Structural and spectroscopic investigations into the origin of this effect were conducted, but were inconclusive. However, the importance of the consideration of N-substituents in such systems is highlighted.

Highly diastereoselective reaction of chiral o-[2-(1,3-oxazolidinyl)]benzaldehydes with alkylmetallic reagents: Synthesis of chiral 3-substituted phthalides

Highly diastereoselective reaction of chiral o-[2-(1,3-oxazolidinyl)]benzaldehydes (4-6) with alkylmetallic reagents provides a new synthetic method for chiral 3-alkylphthalides.

ENANTIOSELECTIVE SYNTHESIS OF β-HYDROXY-α-METHYL CARBONYL COMPOUNDS BY ALDOL REACTION

The enantioselective aldol reactions of ketone lithium enolates with aldehydes mediated chiral lithium amides were extensively investigated.The chiral amino ethers 4a-4l and diamines 16a,b were prepared from α-amino acids.The reaction conditions and the s