250672-66-3

Upstream product

• 25274-94-6 sec-butyl (2E)-3-(1-trityl-1H-imidazol-4-yl)acrylate 
• 25206-11-5 sec-butyl 2-(1-trityl-1H-imidazol-4-yl)cyclopropanecarboxylate 
• 408348-46-9 (1R,2R)-2-(tert-butyldiphenylsilyloxy)methyl-1-(1-triphenylmethyl-1H-imidazol-4-yl)cyclopropane 
• 76-83-5 trityl chloride 
• 3465-72-3 urocanic Acid 
• 25274-93-5 sec-butyl (2E)-3-(1H-imidazol-4-yl)acrylate 
• 201669-70-7 ((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-[(1R,2R)-2-(1-trityl-1H-imidazol-4-yl)-cyclopropyl]-methanone 
• 408348-48-1 (1R,2R)-2-hydroxymethyl-1-(1-triphenylmethyl-1H-imidazol-4-yl)cyclopropane 

Downstream Products

• 201669-72-9 (1R,2R)-1-(1-triphenylmethyl-1H-imidazol-4-yl)cyclopropane-2-carboxylic acid 
• 223419-91-8 (1R,2R)-4-(2-ethynylcyclopropyl)-1-(triphenylmethyl)imidazole 
• 910630-36-3 (1R,2S)-2-formylmethyl-1-(1-triphenylmethyl-1H-imidazol-4-yl)cyclopropane 
• 681807-00-1 (1R,2S)-1-(1-triphenylmethyl-1H-imidazol-4-yl)-2-cyclopropaneacetic acid 
• 910630-39-6 (1R,2S)-N-(4-chlorobenzyl)-1-(1-triphenylmethyl-1H-imidazol-4-yl)-2-cyclopropanacetamide 
• 910630-40-9 (1R,2S)-N-(cyclohexylmethyl)-1-(triphenylmethyl-1H-imidazol-4-yl)-2-cyclopropanacetamide 
• 223419-88-3 4-((1R,2R)-2-(5,5-dimethyl-hex-1-yn-1-yl)-cyclopropyl)-1-trityl-1H-imidazole 
• 524696-02-4 (1R,2R)-2-azidocarbonyl-1-(1-triphenylmethyl-1H-imidazol-4-yl)cyclopropane 
• 524696-04-6 (1S,2S)-2-azidocarbonyl-1-(1-triphenylmethyl-1H-imidazol-4-yl)cyclopropane 
• 524696-09-1 (1R,2R)-2-(t-butyloxycarbonylamino)-1-(1-triphenylmethyl-1H-imidazol-4-yl)cyclopropane 
• 524696-10-4 (1S,2S)-2-(t-butyloxycarbonylamino)-1-(1-triphenylmethyl-1H-imidazol-4-yl)cyclopropane 

Relevant academic research and scientific papers

An Efficient Multigram Synthesis of the Potent Histamine H3 Antagonist GT-2331 and the Reassessment of the Absolute Configuration

GT-2331 is a potent histamine H3 antagonist which has entered clinical trials. Efficient multigram syntheses of this compound and its enantiomer are described. The literature reports that GT-2331 is the dextrorotatory (+), more potent, enantiom

Development of versatile cis- and trans-dicarbon-substituted chiral cyclopropane units: Synthesis of (1S,2R)- and (1R,2R)-2-aminomethyl-1-(1H-imidazol-4-yl)cyclopropanes and their enantiomers as conformationally restricted analogues of histamine

The cyclopropane ring can be used effectively in restricting the conformation of biologically active compounds to improve activity and also to investigate bioactive conformations. We designed (1S,2R)- and (1R,2R)-2-aminomethyl-1-(1H-imidazol-4-yl)cyclopropanes (1 and 2, respectively) and their enantiomers (ent-1 and ent-2) as conformationally restricted analogues of histamine. The four types of chiral cyclopropanes bearing two differentially functionalized carbon substituents in a cis or trans relationship on a cyclopropane ring, (1S,2R)-2-(tert-butyldiphenylsilyloxy)methyl-1-formyl-cyclopropane (7) and (1R,2R)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane (8) and their enantiomers (ent-7 and ent-8), were developed as the key intermediates for synthesizing 1, 2, ent-1, and ent-2. The reaction between (R)-epichlorohydrin [(R)-12] and phenylsulfonylacetonitrile (13a) in the presence of NaOEt in EtOH followed by treatment with acid gave the chiral cyclopropane lactone 11a with 98% ee in 82% yield. Compound 11a was converted into both the cis- and transchiral cyclopropane units 7 and 8, respectively, via reductive desulfonylation with Mg/MeOH as the key step. The corresponding enantiomers, the cis-substituted ent-7 and the trans-substituted ent-8, were also prepared starting from (S)-epichlorohydrin [(S)-12]. The four conformationally restricted target histamine analogues 1, 2, ent-1, and ent-2 were successfully synthesized from 7, 8, ent-7, and ent-8, respectively. The chiral cyclopropane units 7, 8, ent-7, and ent-8 should be useful as versatile intermediates for synthesizing various compounds having an asymmetric cyclopropane structure.