1364780-88-0

Basic information

• Product Name: C₁₆H₂₂LiNO₂
• CAS NO: 1364780-88-0
• Molecular Weight: 267.297
• Mol File: 1364780-88-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: C₁₆H₂₂LiNO₂(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₆H₂₂LiNO₂(1364780-88-0)
• EPA Substance Registry System: C₁₆H₂₂LiNO₂(1364780-88-0)

Safety Data

• Hazardous Substances Data: 1364780-88-0(Hazardous Substances Data)

Upstream product

• 75844-69-8 t-butyl piperidinecarboxylate 
• 154874-89-2 tert-butyl 2-phenylipiperidine-1-carboxylate 
• 591-51-5 phenyllithium 
• 3466-80-6 2-phenylpiperidine 
• 5414-21-1 5-bromopentan-1-nitrile 
• 57050-07-4 2-phenyl-3,4,5,6-tetrahydropyridine 

Downstream Products

• 1364781-74-7 tert-butyl 2-(methoxymethyl)-2-phenylpiperidine-1-carboxylate 
• 1364781-95-2 1-tert-butyl 2-methyl 2-phenylpiperidine-1,2-dicarboxylate 
• 1364781-79-2 tert-butyl 2-(3-methylbut-2-enyl)-2-phenylpiperidine-1-carboxylate 
• 1395055-66-9 (2R)-tert-butyl 2-methyl-2-phenylpiperidine-1-carboxylate 
• 1395055-67-0 C₁₉H₃₁NO₂Si 
• 1395055-68-1 (2R)-1-tert-butyl 2-ethyl 2-phenylpiperidine-1,2-dicarboxylate 
• 1395055-69-2 C₁₅H₁₃⁽²⁾H₆NO₂ 
• 1395055-83-0 C₁₆H₂₂⁽²⁾HNO₂ 
• 1272031-55-6 (R)-2-methyl-2-phenylpiperidine 
• 1395055-70-5 C₁₉H₂₇NO₂ 
• 1395055-71-6 C₂₃H₂₉NO₂ 
• 1364781-69-0 tert-butyl 2-butyl-2-phenylpiperidine-1-carboxylate 

Relevant articles and documents

Synthesis and kinetic resolution of N-Boc-2-arylpiperidines

The chiral base n-BuLi/(-)-sparteine or n-BuLi/(+)-sparteine surrogate promotes kinetic resolution of N-Boc-2-arylpiperidines by asymmetric deprotonation. The enantioenriched starting material was recovered with yields 39-48% and ers up to 97:3. On lithiation then electrophilic quench, 2,2-disubstituted piperidines were obtained with excellent yields and enantioselectivities.

An experimental and in situ IR spectroscopic study of the lithiation-substitution of N-Boc-2-phenylpyrrolidine and -piperidine: Controlling the formation of quaternary stereocenters

A general and enantioselective synthesis of 2-substituted 2-phenylpyrrolidines and -piperidines, an important class of pharmaceutically relevant compounds that contain a quaternary stereocenter, has been developed. The approach involves lithiation-substitution of enantioenriched N-Boc-2-phenylpyrrolidine or -piperidine (prepared by asymmetric Negishi arylation or catalytic asymmetric reduction, respectively). The combined use of synthetic experiments and in situ IR spectroscopic monitoring allowed optimum lithiation conditions to be identified: n-BuLi in THF at -50 °C for 5-30 min. Monitoring of the lithiation using in situ IR spectroscopy indicated that the rotation of the tert-butoxycarbonyl (Boc) group is slower in a 2-lithiated pyrrolidine than a 2-lithiated piperidine; low yields for the lithiation-substitution of N-Boc-2-phenylpyrrolidine at -78 °C can be ascribed to this slow rotation. For N-Boc-2-phenylpyrrolidine and -piperidine, the barriers to rotation of the Boc group were determined using density functional theory calculations and variable-temperature 1H NMR spectroscopy. For the pyrrolidine, the half-life (t1/2) for rotation of the Boc group was found to be ～10 h at -78 °C and ～3.5 min at -50 °C. In contrast, for the piperidine, t1/2 was determined to be ～4 s at -78 °C.