1018909-84-6

Basic information

• Product Name: (3'R,4'R)-tert-butyl 3'-{{6''-[benzyl(tert-butoxycarbonyl)-amino]-4''-methylpyridin-2''-yl}methyl}-4'-hydroxypyrrolidine-1'carboxylate
• Synonyms: (3'R,4'R)-tert-butyl 3'-{{6''-[benzyl(tert-butoxycarbonyl)-amino]-4''-methylpyridin-2''-yl}methyl}-4'-hydroxypyrrolidine-1'carboxylate
• CAS NO: 1018909-84-6
• Molecular Weight: 497.635
• Mol File: 1018909-84-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (3'R,4'R)-tert-butyl 3'-{{6''-[benzyl(tert-butoxycarbonyl)-amino]-4''-methylpyridin-2''-yl}methyl}-4'-hydroxypyrrolidine-1'carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (3'R,4'R)-tert-butyl 3'-{{6''-[benzyl(tert-butoxycarbonyl)-amino]-4''-methylpyridin-2''-yl}methyl}-4'-hydroxypyrrolidine-1'carboxylate(1018909-84-6)
• EPA Substance Registry System: (3'R,4'R)-tert-butyl 3'-{{6''-[benzyl(tert-butoxycarbonyl)-amino]-4''-methylpyridin-2''-yl}methyl}-4'-hydroxypyrrolidine-1'carboxylate(1018909-84-6)

Safety Data

• Hazardous Substances Data: 1018909-84-6(Hazardous Substances Data)

Upstream product

• 1221065-00-4 (3R,4R)-tert-butyl 3-((6-(tert-butoxycarbonylamino)-4-methylpyridin-2-yl)methyl)-4-(tert-butoxycarbonyloxy)pyrrolidine-1-carboxylate 
• 100-39-0 benzyl bromide 
• 848472-36-6 tert-butyl (4,6-dimethylpyridin-2-yl)carbamate 
• 114214-49-2 1-tert-butoxycarbonyl-3,4-epoxypyrrolidine 
• 5407-87-4 2-Amino-4,6-dimethylpyridine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 73286-70-1 N-(tert-butoxycarbonyl)-3-pyrroline 
• 1018909-82-4 (3R,4R)-tert-butyl 3-{{6-[benzyl(tert-butoxycarbonyl)amino]-4-methylpyridin-2-yl}methyl}-4-{(1S,4R)-4,7,7-trimethyl-3-oxo-oxabicyclo[2.2.1]heptane-1-carbonyloxy}pyrrolidine-1-carboxylate 

Downstream Products

• 1018910-03-6 (3S,4R)-tert-butyl 3-azido-4-{{6-[benzyl(tert-butoxycarbonyl)amino]-4-methylpyridin-2-yl}methyl}-4-hydroxypyrrolidine-1-carboxylate 
• 1018909-86-8 (3'S,4'R)-tert-butyl 3'-acetoxy-4'-{{6''-[benzyl(tert-butoxycarbonyl)amino]-4''-methylpyridin-2''-yl}methyl}pyrrolidine-1'-carboxylate 
• 1386976-20-0 C₃₂H₄₄FN₃O₅ 
• 1386976-05-1 C₃₂H₄₃ClFN₃O₅ 
• 1386976-22-2 C₃₂H₄₆FN₃O₅ 
• 1386976-08-4 C₃₂H₄₅ClFN₃O₅ 
• 1386976-11-9 tert-butyl (3R,4R)-3-((6-((tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-(4-(3-chloro-5-fluorophenoxy)butoxy)pyrrolidine-1-carboxylate 
• 1018910-13-8 (3'R,4'R)-tert-butyl 3'-(allyloxy)-4'-{{6''-[benzyl(tert-butoxycarbonyl)amino]-4''-methylpyridin-2''-yl}methyl}pyrrolidine-1'-carboxylate 

Relevant articles and documents

An alkoxide anion-triggered tert-butyloxycarbonyl group migration. Mechanism and application

We report a fast N→O tert-butyloxycarbonyl (Boc) migration of the imide (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-hyd roxypyrrolidine-1-carboxylate (2) via a base-generated alkoxide. The mechanism of the migration is intramolecular, involving an unusual nine-membered cyclic transition state.

Exploration of the active site of neuronal nitric oxide synthase by the design and synthesis of pyrrolidinomethyl 2-aminopyridine derivatives

Neuronal nitric oxide synthase (nNOS) represents an important therapeutic target for the prevention of brain injury and the treatment of various neurodegenerative disorders. A series of trans-substituted amino pyrrolidinomethyl 2-aminopyridine derivatives

Potent, highly selective, and orally bioavailable gem-difluorinated monocationic inhibitors of neuronal nitric oxide synthase

In our efforts to discover neuronal isoform selective nitric oxide synthase (NOS) inhibitors, we have developed a series of compounds containing a pyrrolidine ring with two stereogenic centers. The enantiomerically pure compounds, (S,S) versus (R,R), exhibited two different binding orientations, with (R,R) inhibitors showing much better potency and selectivity. To improve the bioavailability of these inhibitors, we have introduced a CF2 moiety geminal to an amino group in the long tail of one of these inhibitors, which reduced its basicity, resulting in compounds with monocationic character under physiological pH conditions. Biological evaluations have led to a nNOS inhibitor with a Ki of 36 nM and high selectivity for nNOS over eNOS (3800-fold) and iNOS (1400-fold). MM-PBSA calculations indicated that the low pKa NH is, at least, partially protonated when bound to the active site. A comparison of rat oral bioavailability of the difluorinated compound to the parent molecule shows 22% for the difluorinated compound versus essentially no oral bioavailability for the parent compound. This indicates that the goal of this research to make compounds with only one protonated nitrogen atom at physiological pH to allow for membrane permeability, but which can become protonated when bound to NOS, has been accomplished.