70489-63-3

Usage

Type of compound

Tertiary amino alcohol

Structure

Branched, containing a butyl group, a hydroxyl group, and an amino group

Applications

a. Chiral building block in the synthesis of pharmaceuticals and agrochemicals
b. Intermediate in the production of surfactants and corrosion inhibitors
c. Potential application in asymmetric catalysis
d. Reagent for the synthesis of amino-acid derivatives

Importance

Versatile intermediate chemical with diverse applications in various industries

Upstream product

• 2245-30-9 1,2-epoxy-3,3-dimethylbutane 
• 88522-73-0 trimethylacetaldehyde cyanohydrin trimethylsilyl ether 
• 33350-17-3 (R)-2-hydroxy-3,3-dimethylbutanenitrile 
• 630-19-3 pivalaldehyde 
• 58054-88-9 3,3-dimethyl-1-nitrobutan-2-ol 
• 33350-17-3 2-hydroxy-3,3-dimethylbutyronitrile 
• 157135-73-4 (+/-)-1-Azido-3,3-dimethyl-2-butanol 

Downstream Products

• 167888-42-8 (R)-2-[N-(3'-tert-butylsalicylidene)amino]-3,3-dimethyl-2-butanol 
• 185426-15-7 (±)-tert-butyl (2-hydroxy-3,3-dimethylbutyl)carbamate 

Relevant academic research and scientific papers

KINASE INHIBITORS AND USES THEREOF

Provided are cyclic iminopyridimdine compounds and their bicyclic derivatives, pharmaceutical compositions comprising such compounds, and methods of using such compounds or compositions, such as methods of treating a proliferation disorder, such as a cancer or a tumor, or in some embodiments disease or disorders related to the dysregulation of kinase such as, but not limited to kinases such as MAPK, PDGFR, Src, PAKs, c-Kit, EphA2, EphB4, FGFR, Axl, and c-Met.

Chiral-Organotin-Catalyzed Kinetic Resolution of Vicinal Amino Alcohols

A highly efficient kinetic resolution of racemic amino alcohols has been achieved for the first time with a chiral tin catalyst. A chiral organotin compound with 3,4,5-trifluorophenyl groups at the 3,3′-positions of the binaphthyl framework enabled this transformation with excellent yield and high enantioselectivity. The process tolerates aryl- and alkyl-substituted amino alcohols and a variety of other substrates, affording the corresponding products in high enantioselectivity and with s factors up to >500.

Substituted pyrazolo-piperazines as casein kinase 1 δ/ε inhibitors

The invention provides compounds of Formula (I): and pharmaceutically acceptable salts thereof. The compounds of Formula (I) inhibit protein kinase activity thereby making them useful as anticancer agents.

Use of a Catalytic Chiral Leaving Group for Asymmetric Substitutions at sp3-Hybridized Carbon Atoms: Kinetic Resolution of β-Amino Alcohols by p-Methoxybenzylation

A catalytic strategy was developed for asymmetric substitution reactions at sp3-hybridized carbon atoms by using a chiral alkylating agent generated in situ from trichloroacetimidate and a chiral phosphoric acid. The resulting chiral p-methoxybenzyl phosphate selectively reacts with β-amino alcohols rather than those without a β-NH functionality. The use of an electronically and sterically tuned chiral phosphoric acid enables the kinetic resolution of amino alcohols through p-methoxybenzylation with good enantioselectivity.

Kinetic resolution of racemic amino alcohols through intermolecular acetalization catalyzed by a chiral Bronsted acid

The kinetic resolution of racemic secondary alcohols is a fundamental method for obtaining enantiomerically enriched alcohols. Compared to esterification, which is a well-established method for this purpose, kinetic resolution through enantioselective intermolecular acetalization has not been reported to date despite the fact that the formation of acetals is widely adopted to protect hydroxy groups. By taking advantage of the thermodynamics of acetalization by the addition of alcohols to enol ethers, a highly efficient kinetic resolution of racemic amino alcohols was achieved for the first time and in a practical manner using a chiral phosphoric acid catalyst.

Catalyst development for organocatalytic hydrosilylation of aromatic ketones and ketimines

A new family of Lewis basic 2-pyridyl oxazolines have been developed, which can act as efficient organocatalysts for the enantioselective reduction of prochiral aromatic ketones and ketimines with trichlorosilane, a readily available and inexpensive reagent. 1-Isoquinolyl oxazoline, derived from mandelic acid, was identified as the most efficient catalyst of the series, capable of delivering high enantioselectivities in the reduction of both ketones (up to 94% ee) and ketimines (up to 89% ee).

Synthesis of tri- and tetrasubstituted imidazoles

A reliable sequence that allows for regiospecific incorporation of four alkyl substituents on an imidazole ring has been developed. This procedure involves the addition of a substituted amino alcohol to a thioamide and subsequent oxidation with PDC. Unlike many imidazole syntheses, acid-sensitive functionality is tolerated given the mild conditions.

ORGANIC COMPOUNDS

Compounds of Formula (I); in free or salt form, wherein Ra, Rb, R2, R3, R4 and R5 have the meanings as indicated in the specification, are useful for treating conditions that are mediated by mediated by phosphatidylinositol 3-kinase. Pharmaceutical compositions that contain the compounds and a process for preparing the compounds are also described.

A Convenient Route to (R)-α-Hydroxy Carboxylic Acids and (2R)-1-Amino-2-alkanols from (R)-Cyanohydrins

(R)-Cyanohydrins, prepared in good to excellent yields with high optical purity by enzyme-catalyzed addition of hydrogen cyanide to aldehydes in organic solvents, are hydrolyzed with concentrated hydrochloric acid at ambient temperature, usually in very high yield, without any trace of racemization to give (R)-α-hydroxy carboxylic acids.Likewise, no racemization is observed by direct reduction of the (R)-cyanohydrins with lithium aluminium hydride to give (2R)-1-amino-2-alkanols.