467454-33-7Relevant academic research and scientific papers
BICYCLIC PROLINE COMPOUNDS
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Paragraph 0163-0166, (2018/02/22)
The invention is concerned with the compounds of formula (I) and salts thereof. In addition, the present invention relates to methods of manufacturing and methods of using the compounds of formula (I) as well as pharmaceutical compositions containing such compounds. The compounds may be useful in treating diseases and conditions mediated by TRPA1, such as pain.
Preparation of 2-Azabicyclo[21.1]hexane Hydrochloride
Liao, Haili,Li, Aimin,Chen, Xingsong,Liang, Kun,Shen, Yang,Liang, Qingfeng,Xu, Kewei,Shore, Daniel G. M.,Villemure, Elisia,Siu, Michael,Huestis, Malcolm P.
supporting information, p. 2251 - 2253 (2016/11/14)
A batchwise, multigram preparation of 2-azabicyclo-[2.1.1]hexane hydrochloride (1·HCl) was developed, delivering a total of 195 grams of material. The key synthetic step involves an intramolecular displacement of a primary alkyl chloride with a tert-butylsulfinamide to forge the [2.1.1]-bicyclic ring system.
5-Carboxy-2-azabicyclo[2.1.1]hexanes as precursors of 5-halo, amino, phenyl, and 2-methoxycarbonylethyl methanopyrrolidines
Krow, Grant R.,Huang, Qiuli,Lin, Guoliang,Centafont, Ryan A.,Thomas, Andrew M.,Gandla, Deepa,DeBrosse, Charles,Carroll, Patrick J.
, p. 2090 - 2098 (2007/10/03)
Novel 5-X-substituted-2-azabicyclo[2.1.1]hexanes (X = 5-syn-Cl, -Br, -I, -Ph, -NHCOOR (R = Me, Bn, t-Bu), -CH2CH2COOMe and X = 5-anti-Br, -I, -Ph) were synthesized from the X = 5-syn-carboxy derivative. New 5-anti-X-2-azabicyclo[2.1.
Convenient preparations of 2,4-methanopyrrolidine and 5-carboxy-2,4-methanopyrrolidines
Krow, Grant R.,Lin, Guoliang,Herzon, Seth B.,Thomas, Andrew M.,Moore, Keith P.,Huang, Qiuli,Carroll, Patrick J.
, p. 7562 - 7564 (2007/10/03)
An efficient four-step synthesis of N-BOC-5-syn- and 5-anti-carboxymethanopyrrolidines (12 and 13) and the conversion of 12 to N-BOC-methanopyrrolidine (2) are described.
Complex-induced proximity effects. Temperature-dependent regiochemical diversity in lithiation-electrophilic substitution reactions of N-BOC-2-azabicyclo[2.1.1]hexane. 2,4- and 3,5-methanoprolines.
Krow, Grant R,Herzon, Seth B,Lin, Guoliang,Qiu, Feng,Sonnet, Philip E
, p. 3151 - 3154 (2007/10/03)
[reaction: see text] Azabicycle 4 and sec-butyllithium/TMEDA afford the C(1) bridgehead alpha-lithio anion at 0 degrees C. Anion quenching with carbon dioxide, methyl chloroformate, or DMF provide the bridgehead acid 8a (N-BOC-2,4-methanoproline), ester 8b, or aldehyde 8c, respectively. By contrast, at -78 degrees C these same reagents give a mixture of regioisomeric methylene and bridgehead anions whose quenching leads to mixtures of regioisomeric methylene and bridgehead acids 6a/8a, esters 6b/8b, or aldehydes 6c/8c, respectively. The previously unknown 3,5-methanoproline was prepared as its N-BOC methyl ester 6b.
