Home Chemistry Heterocyclic Building Blocks Pyrrolidines (R)-3-Phenylpyrrolidine
Nucleophilic Substitution: (R)-3-phenylpyrrolidine contains a nucleophilic amine group. It can undergo nucleophilic substitution reactions, where the nitrogen atom can be attacked by electrophiles. For example, it can react with alkyl halides to form N-alkylated products.
Ring Opening: The pyrrolidine ring can be opened under specific conditions, such as strong acids or bases, leading to the formation of open-chain compounds. This can be useful in synthesis strategies.
Amide Formation: The amine group in (R)-3-phenylpyrrolidine can react with acid chlorides or anhydrides to form amides.
Reduction: The ketone group in (R)-3-phenylpyrrolidine can be reduced to the corresponding alcohol using reducing agents like sodium borohydride (NaBH4) or lithium aluminum hydride (LiAlH4).
Ring-closing Reactions: Depending on the reaction conditions and reagents, (R)-3-phenylpyrrolidine can participate in various ring-closing reactions to form different cyclic compounds.
Enantioselective Reactions: Due to its chiral nature, (R)-3-phenylpyrrolidine can be used as a chiral auxiliary or catalyst in enantioselective reactions to control the stereochemistry of the products.
Aromatic Substitution: The phenyl group in (R)-3-phenylpyrrolidine can undergo electrophilic aromatic substitution reactions, such as Friedel-Crafts acylation or alkylation, to introduce substituents onto the aromatic ring.
Oxidation: The organic groups in (R)-3-phenylpyrrolidine can be oxidized to produce various functional groups depending on the choice of oxidizing agent. For instance, the phenyl group can be oxidized to a carboxylic acid or an alcohol.
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(3S,4R)-4-(3-Chlorophenyl)pyrrolidine-3-carboxylic acid
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(3S,4R)-4-Phenylpyrrolidine-3-carboxylic acid hydrochloride
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tert-Butyl (3S,4R)-3-amino-4-phenylpyrrolidine-1-carboxylate
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(3S,4R)-1-tert-Butyl-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylic acid
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rel-(3S,4R)-1-(tert-Butoxycarbonyl)-4-(4-(trifluoromethyl)phenyl)pyrrolidine-3-carboxylic acid
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