156038-84-5 Usage
Description
(S,S)-N-Boc-2,5-dimethylpyrrolidine, with the molecular formula C13H25NO2, is an N-Boc-protected, chiral pyrrolidine derivative. It is a chemical compound that features a Boc (tert-butoxycarbonyl) group attached to the nitrogen atom of the pyrrolidine ring. (S,S)-N-Boc-2,5-dimethylpyrrolidine is highly valued in the field of organic synthesis and pharmaceutical research due to its unique structure and chirality, making it a versatile intermediate for the preparation of various biologically active compounds and pharmaceutical agents.
Uses
Used in Pharmaceutical Research:
(S,S)-N-Boc-2,5-dimethylpyrrolidine is used as a building block for the synthesis of biologically active compounds and pharmaceutical agents. Its unique structure and chirality make it a valuable intermediate in the development of chiral drug molecules and complex organic compounds, contributing to advancements in medicinal chemistry and drug development.
Used in Organic Synthesis:
In the field of organic synthesis, (S,S)-N-Boc-2,5-dimethylpyrrolidine serves as a crucial component for creating a wide range of chemical compounds. Its N-Boc protection and chiral nature allow for selective reactions and the formation of specific target molecules, enhancing the efficiency and precision of organic synthesis processes.
Check Digit Verification of cas no
The CAS Registry Mumber 156038-84-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,6,0,3 and 8 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 156038-84:
(8*1)+(7*5)+(6*6)+(5*0)+(4*3)+(3*8)+(2*8)+(1*4)=135
135 % 10 = 5
So 156038-84-5 is a valid CAS Registry Number.
156038-84-5Relevant articles and documents
Complex induced proximity effects: Enantioselective syntheses based on asymmetric deprotonations of N-Boc-pyrrolidines
Beak, Peter,Kerrick, Shawn T.,Wu, Shengde,Chu, Jingxi
, p. 3231 - 3239 (2007/10/02)
Lithiation of N-Boc-pyrrolidine (6) with sec-butyllithium (s-BuLi)/(-)-sparteine (14) effects an asymmetric deprotonation to give (S)-2-lithio-N-Boc-pyrrolidine ((S)-22), which reacts with electrophiles to provide the 2-substituted N-Boc-pyrrolidines 7-11 and 13 in enantiomeric excesses which generally are >90%. In the lithiation-silylation of 6 the chiral ligand 15 gives 7 with a lower enantiomeric excess and chiral ligands 16 and 17 give 7 with lower and opposite enantiomeric excesses than that obtained with 14. Diastereoselective amplification operates in a sequential lithiation-substitution sequence to provide the conversion of (S)-2-methyl-N-Boc-pyrrolidine ((S)-10) of 95% enantiomeric excess with s-BuLi/14 to (S,S)-2,5-dimethyl-N-Boc-pyrrolidine ((S,S)-19) with >99% enantiomeric excess. Synthetic preparations of a useful chiral ligand, (R)-α,α-diphenyl-2-pyrrolidine ((R)-20), and a useful chiral auxiliary, (S,S)-2,5-dimethylpyrrolidine hydrochloride ((S,S)-21), are reported. Reactions of racemic and enantioenriched 2-lithio-N-Boc-pyrrolidine and investigation of sequential lithiations-deuterations of 6 establish the reaction pathway to be asymmetric deprotonation rather than asymmetric substitution. A rationalization for the enantioselective deprotonation is provided.
