154874-88-1

Basic information

• Product Name: 1-Pyrrolidinecarboxylic acid, 2-phenyl-, 1,1-dimethylethyl ester
• Synonyms: N-Boc 2-phenyl pyrrolidine;1,1-dimethylethyl 2-(phenyl)-1-pyrrolidinecarboxylate;tert-butyl 2-phenyl-1-pyrrolidinecarboxylate;1-(t-butoxycarbonyl)-2-phenylpyrrolidine;2-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester;N-(tert-butoxycarbonyl)-2-phenylpyrrolidine;(R)-N-Boc-2-phenylpyrrolidine
• CAS NO: 154874-88-1
• Molecular Formula: C15H21NO2
• Molecular Weight: 247.337
• Mol File: 154874-88-1.mol
• Article Data: 32

Chemical Properties

• CAS DataBase Reference: 1-Pyrrolidinecarboxylic acid, 2-phenyl-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pyrrolidinecarboxylic acid, 2-phenyl-, 1,1-dimethylethyl ester(154874-88-1)
• EPA Substance Registry System: 1-Pyrrolidinecarboxylic acid, 2-phenyl-, 1,1-dimethylethyl ester(154874-88-1)

Safety Data

• Hazardous Substances Data: 154874-88-1(Hazardous Substances Data)

Upstream product

• 591-50-4 iodobenzene 
• 1006-64-0 2-(phenyl)pyrrolidine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 108-86-1 bromobenzene 
• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 
• 824-90-8 1-phenylbut-1-ene 
• 84473-31-4 4-(Bromobutyl)benzene 
• 27126-25-6 α-azidophenylbutane 
• 13633-25-5 1-Bromo-4-phenylbutane 
• 3592-47-0 Benzaldehyde-d 
• 170491-63-1 N-Boc-prolinol 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 1078-58-6 diphenylzinc 
• 15761-39-4 N-tert-butoxycarbonyl-proline 

Downstream Products

• 116437-41-3 tert-butyl (4-oxo-4-phenyl-butyl)-carbamate 
• 1364782-59-1 C₁₆H₂₁NO₄ 
• 1364781-17-8 2-phenyl pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 1364782-63-7 (S)-2-phenyl-2-phenylcarbamoylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 1364782-68-2 (R)-2-phenyl-2-phenylcarbamoylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 1364781-57-6 1,1,7a-triphenyltetrahydropyrrolo[1,2-c]oxazol-3-one 
• 1364781-52-1 2-phenyl-2-trimethylsilanylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 1364781-43-0 2-allyl-2-phenylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 1364781-30-5 2-phenyl-2-phenylcarbamoylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 137496-67-4 N-tert-butoxycarbonyl-2-trimethylsilylpyrrolidine 

Relevant articles and documents

Application of [Co(Corrole)]– Complexes in Ring-Closing C–H Amination of Aliphatic Azides via Nitrene Radical Intermediates

The synthesis, characterisation and application of anionic [CoII(Cor)]– (Cor = corrole) metalloradicals in the ring-closing C–H amination of an aliphatic azide in the presence of Boc2O (Boc = tert-butyloxycarbonyl) to give the corresponding Boc-protected N-heterocyclic product tert-butyl 2-phenylpyrrolidine-1-carboxylate are reported. This is the first example of the use of metalloradical cobalt(II) corrole complexes in nitrene-transfer reactions. On the basis of DFT calculations, the reaction is proposed to proceed via discrete open-shell nitrene radical intermediates bearing most of their spin density at the nitrene nitrogen atom. The [CoII(Cor)]– complexes are substantially faster catalysts than the corresponding neutral [CoII(porphyrin)] complexes when applied in the same ring-closing C–H amination reaction under identical reaction conditions. Increasing the electron density at cobalt(II) therefore has a positive influence on the reaction rate.

A facile route to 2-substituted N-Boc pyrrolidines

Dipole stabilized carbanion 2 cyclizes to afford the key intermediate 2-benzotriazolyl-N-Boc-pyrrolidine 3, which undergoes nucleophilic displacement of the benzotriazolyl group to afford various 2-substituted-N-Boc-pyrrolidines in good yields. (C) 2000 P

Copper cyanide catalyzed palladium coupling of α-lithio amines and aryl iodides

Treatment of α-aminoalkyllithium reagents with aryl iodides in the presence of catalytic amounts of CuCN and PdCl2(PPh3)2 or [(p-MeOC6H4)3P]4Pd affords 2-aryl substituted amines in modest to good yields. Coupled products are obtained with electron rich aryl iodides and the reaction fails with electron poor aryl halides.

Photocatalytic Dehydroxymethylative Arylation by Synergistic Cerium and Nickel Catalysis

Under mild reaction conditions with inexpensive cerium and nickel catalysts, easily accessible free alcohols can now be utilized as operationally simple and robust carbon pronucleophiles in selective C(sp3)-C(sp2) cross-couplings. Facilitated by automated high-throughput experimentation, sterically encumbered benzoate ligands have been identified for robust cerium complexes, enabling the synergistic cooperation of cerium catalysis in the emerging metallaphotoredox catalysis. A broad range of free alcohols and aromatic halides can be facilely employed in this transformation, representing a new paradigm for the C(sp3)-C(sp2) bond construction between free alcohols and aryl halides with the extrusion of formaldehyde. Moreover, mechanistic investigations have been conducted, leading to the identification of a tribenzoate cerium(III) complex as a viable intermediate.

O-benzoylhydroxylamines as alkyl nitrene precursors: Synthesis of saturated N-heterocycles from primary amines

We introduce O-benzoylhydroxylamines as competent alkyl nitrene precursors. The combination of readily available, stable substrates and a proficient rhodium catalyst provides a straightforward means for the construction of various pyrrolidine rings from the corresponding primary amines. Preliminary mechanistic investigation suggests that the structure of the nitrene precursor plays a role in determining the nature of the resulting reactive intermediate.