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 
• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 
• 591-51-5 phenyllithium 
• 108-86-1 bromobenzene 
• 170491-63-1 N-Boc-prolinol 
• 3592-47-0 Benzaldehyde-d 
• 13633-25-5 1-Bromo-4-phenylbutane 
• 27126-25-6 α-azidophenylbutane 
• 24424-99-5 di-tert-butyl dicarbonate 
• 84473-31-4 4-(Bromobutyl)benzene 
• 824-90-8 1-phenylbut-1-ene 
• 1078-58-6 diphenylzinc 
• 15761-39-4 N-tert-butoxycarbonyl-proline 
• 98-80-6 phenylboronic acid 

Downstream Products

• 137496-67-4 N-tert-butoxycarbonyl-2-trimethylsilylpyrrolidine 
• 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 

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.

Dumbbell-Shaped 2,2’-Bipyridines: Controlled Metal Monochelation and Application to Ni-Catalyzed Cross-Couplings

2,2’-Bipyridine ligands (dsbpys) with dumbbell-like shapes and differently substituted triarylmethyl groups at the C5 and C5’ positions showed high ligand performance in the Ni-catalyzed cross-electrophile coupling and the Ni/photoredox-synergistically catalyzed decarboxylative coupling reactions. The superior ligand effects of dsbpys compared to the conventional bpy ligands were attributed to the monochelating nature of dsbpys.

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.