246510-69-0

Basic information

• Product Name: (3S,4S)-1-N-CBZ-3-(N-BOC-AMINO)-4-HYDROXYMETHYLPYRROLIDINE
• Synonyms: (3S,4S)-1-N-CBZ-3-(N-BOC-AMINO)-4-HYDROXYMETHYLPYRROLIDINE;benzyl 3-(tert-butoxycarbonylamino)-4-(hydroxymethyl)pyrrolidine-1-carboxylate
• CAS NO: 246510-69-0
• Molecular Formula: C₁₈H₂₆N₂O₅
• Molecular Weight: 350.412
• Mol File: 246510-69-0.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3S,4S)-1-N-CBZ-3-(N-BOC-AMINO)-4-HYDROXYMETHYLPYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S)-1-N-CBZ-3-(N-BOC-AMINO)-4-HYDROXYMETHYLPYRROLIDINE(246510-69-0)
• EPA Substance Registry System: (3S,4S)-1-N-CBZ-3-(N-BOC-AMINO)-4-HYDROXYMETHYLPYRROLIDINE(246510-69-0)

Safety Data

• Hazardous Substances Data: 246510-69-0(Hazardous Substances Data)

Usage

General Description

"(3S,4S)-1-N-CBZ-3-(N-BOC-AMINO)-4-HYDROXYMETHYLPYRROLIDINE" is a chemical compound with the molecular formula C15H24N2O4. It is a derivative of pyrrolidine, containing a carbobenzoxy (CBZ) and a tert-butoxycarbonyl (BOC) protecting group on the nitrogen and hydroxyl groups, respectively. (3S,4S)-1-N-CBZ-3-(N-BOC-AMINO)-4-HYDROXYMETHYLPYRROLIDINE is commonly used as a building block in organic synthesis to create complex molecules with specific stereochemical arrangements. It is also used as a chiral ligand in asymmetric catalysis and as a precursor in the synthesis of pharmaceuticals and natural products. Additionally, it has potential applications in the field of medicinal chemistry for the development of new drugs.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 370881-76-8 benzyl (cis)-3-amino-4-(hydroxymethyl)-1-pyrrolidinecarboxylate (S)-mandelate 
• 252770-03-9 Benzyl (4aS,7aS)-2,2-dimethylhexahydropyrrolo[3,4-d][1,3]oxazine-6(4H)-carboxylate (R)-mandelate 
• 569682-60-6 benzyl N-(2,2-dimethoxyethyl)-N-(prop-2-en-1-yl)carbamate 
• 114790-39-5 benzyl N-(2,2-dimethoxyethyl)carbamate 
• 501-53-1 benzyl chloroformate 
• 252770-09-5 benzyl (cis)-3-amino-4-(hydroxymethyl)-1-pyrrolidinecarboxylate 
• 370880-76-5 benzyl N-[2-(hydroxyimino)ethyl]-N-(prop-2-en-1-yl)carbamate 
• 370880-75-4 benzyl N-(2-oxoethyl)-N-(prop-2-en-1-yl)carbamate 
• 252770-08-4 benzyl (cis)-3-amino-4-(hydroxymethyl)-1-pyrrolidinecarboxylate 

Downstream Products

• 246510-70-3 benzyl (3S,4S)-3-tert-butoxycarbonylamino-4-methylsulfonyloxymethyl-pyrrolidine-1-carboxylate 
• 869956-05-8 (3S,4S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-(p-toluenesulfonyloxy)methylpyrrolidine 
• 869956-21-8 (3S,4S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-(phenylsulfanil)methylpyrrolidine 
• 869956-08-1 (3S,4S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-formylpyrrolidine 
• 370881-43-9 benzyl (1S,5S)-3,6-diaza-bicyclo[3.2.0]heptane-3-carboxylate 
• 799279-81-5 (1R,5S)-tert-butyl 3,6-diaza-bicyclo[3.2.0]heptane-6-carboxylate 
• 799279-84-8 (1R,5S)-3-benzyl 6-tert-butyl 3,6-diazabicyclo[3.2.0]heptane-3,6-dicarboxylate 
• 799279-80-4 Sofinicline 
• 799279-83-7 benzyl (3S,4S)-3-(amino)-4-{[(methylsulfonyl)oxy]methyl}-1-pyrrolidinecarboxylate trifluoroacetate 

Relevant articles and documents

Synthesis and structure-activity relationship studies of 3,6-diazabicyclo[3.2.0]heptanes as novel α4β2 nicotinic acetylcholine receptor selective agonists

A series of novel, potent neuronal nicotinic acetylcholine receptor (nAChR) ligands derived from 3,6-diazabicyclo[3.2.0]heptane have been synthesized and evaluated for binding affinity and agonist activity at the α4β2 nAChR subtype. Structure-activity relationship studies of these novel nAChR ligands focused on substitution effects on the pyridine ring, as well as stereo- and regiochemical influences of the 3,6-diazabicyclo[3.2.0]heptane core. Small 5-substituents on the pyridine ring had a modest impact on the binding affinities and functional activities. 6-Bromo, 6-chloro, and 6-methyl substituents on the pyridine ring led to increased binding affinities and improved functional activities. Most of the 6-N-pyridinyl-substituted 3,6-diazabicyclo[3.2.0]heptanes are selective for the α4β2 nAChR subtype. Compounds (1R,5S)-25, (1R,5S)-55, and (1R,5S)-56 were virtually inactive as agonists at the hα3β4 nAChR but retained potency and efficacy at the hα4β2 nAChR subtype. 3-N-Pyridinyl-substituted series demonstrated more complex SAR. (1R,5R)-39, (1R,5R)-41, and (1R,5R)-42 were found to be much more potent at the hα3β4 nAChR subtype, whereas (1R,5R)-38 and (1R,5R)-40 were very selective at the hα4β2 nAChR subtype. The SAR studies of these novel ligands led to the discovery of several compounds with interesting in vitro pharmacological profiles.

Amino-substituted tricyclic derivatives and methods of use

Compounds of formula (I) wherein A and B are amine-substituted sidechains, Y1 and Y2 form various tricyclic cores, and Rx is an optional substituent. Compounds and compositions of formula (I) are contemplated as well as methods for treating conditions or disorders prevented by or ameliorated by α7 nAChR ligands that encompass compounds of formula (I) and other tricyclic derivatives.

Substituted diazabicycloalkane derivatives

Compounds of formula (I) [in-line-formulae]Z-Ar1—Ar2??(I) [/in-line-formulae] wherein Z is a diazabicyclic amine, Ar1 is a 5- or 6-membered aromatic ring, and Ar2 is selected from the group consisting of an unsubstituted or substituted 5- or 6-membered heteroaryl ring; unsubstituted or substituted bicyclic heteroaryl ring; 3,4-(methylenedioxy)phenyl; carbazolyl; tetrahydrocarbazolyl; naphthyl; and phenyl; wherein the phenyl is substituted with 0, 1, 2, or 3 substituents in the meta- or para-positions. The compounds are useful in treating conditions or disorders prevented by or ameliorated by α7 nAChR ligands. Also disclosed are pharmaceutical compositions comprising compounds of formula (I) and methods for using such compounds and compositions.