76735-19-8

Usage

Uses

Used in Organic Synthesis:
(1R,4R,5R,6S)-1,3,3-trimethyl-6-(pyrrolidin-1-yl)-2-oxabicyclo[2.2.2]octan-5-ol is used as a building block in organic synthesis for the creation of more complex molecules. Its unique bicyclic structure and functional groups allow for versatile chemical reactions and the formation of a wide range of organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (1R,4R,5R,6S)-1,3,3-trimethyl-6-(pyrrolidin-1-yl)-2-oxabicyclo[2.2.2]octan-5-ol is used as a potential active pharmaceutical ingredient (API) or as an intermediate in the synthesis of APIs. Its specific stereochemistry and functional groups may contribute to the development of new drugs with unique therapeutic properties.
Used in Material Science:
(1R,4R,5R,6S)-1,3,3-trimethyl-6-(pyrrolidin-1-yl)-2-oxabicyclo[2.2.2]octan-5-ol is utilized in material science for the development of new materials with specific properties. Its unique structure and functional groups can be employed to create materials with tailored characteristics for various applications, such as in coatings, adhesives, or polymers.

Upstream product

• 76735-19-8 (1R,4S,5R,6S)-1,3,3-Trimethyl-6-pyrrolidin-1-yl-2-oxa-bicyclo[2.2.2]octan-5-ol 
• 76735-24-5 1,3,3-trimethyl-6-cis-pyrrolidin-1-yl-2-oxabicyclo<2.2.2>octan-5-one 
• 31316-33-3 1-((1R,4S)-1,3,3-Trimethyl-2-oxa-bicyclo[2.2.2]oct-5-en-6-yl)-pyrrolidine 

Downstream Products

• 76735-19-8 (1R,4S,5S,6S)-1,3,3-Trimethyl-6-pyrrolidin-1-yl-2-oxa-bicyclo[2.2.2]octan-5-ol 

Relevant academic research and scientific papers

Carbonyl Transposition and Regio- and Stereo-specific Syntheses of New Alcohols, Amino-alcohols, and Ketones in the Monoterpenoid 1,3,3-Trimethyl-2-oxabicyclooctane

An efficient transposition of carbonyl group R1-CO-CH2-R2 -> R1-CH2-CO-R2 in the 1,3,3-trimethyl-2-oxabicyclooctane system was carried out via hydroboration-oxidation of 6-dialkylamino-1,3,3-trimethyl-2-oxabicyclooct-5-enes (3a-c), which gave regio- and stereo-specifically 6-cis-dialkylamino-1,3,3-trimethyl-2-oxabicyclooctan-5-trans-ols (4a-c) in high yield.Cope reaction on the N-oxide (5b) obtained from the amino-alcohol (4b) with hydrogen peroxide led to 1,3,3-trimethyl-2-oxabicyclooctan-5-one (6), the other possible isomer of the long-known 1,3,3-trimethyl-2-oxabicyclooctan-6-one (1b).The ketone (6) was also obtained from 1,3,3-trimethyl-2-oxabicyclooct-5-ene (2) via its trans-epoxide (11), lithium aluminium hydride reduction at 160-165 deg C of which gave stereo- and regio-specifically 1,3,3-trimethyl-2-oxabicyclooctan-5-trans-ol (9b).Chromic acid oxidation of (9b) and (4a-c) under various conditions gave the ketone (6) and the amino-ketones (7a-c), respectively.Lithium aluminium hydride reduction of (6) and (7a-c) afforded stereospecifically the cis-alcohol (9a) and 6-cis-dialkylamino-1,3,3-trimethyl-2-oxabicyclooctan-5-cis-ols (8a-c), respetively.Hydroboration-oxidation of the alkene (2) was not regiospecific, giving a 3:1 mixture of the trans-alcohols (9b) and (10b), respectively.