129705-31-3

Upstream product

• 38484-56-9 (+/-)-2,5-hexanediol 
• 124-63-0 methanesulfonyl chloride 
• 2935-44-6 hexane-2,5-diol 

Downstream Products

• 129705-29-9 (2S,5S)-2,5-dimethyl-1-phenylphospholane 
• 137152-02-4 bis(2-((2S,5S)-2,5-dimethylphospholanoethyl))phenylphosphine 
• 136779-26-5 1,2-bis((2S,5S)-2,5-dimethylphospholano)ethane 

Relevant academic research and scientific papers

Asymmetric synthesis of trans-2,5-dimethylpyrrolidine

A new synthetic route to (2S,5S)-dimethylpyrrolidine 1, which can also be applied to the synthesis of the (2R,5R)-enantiomer, has been developed. The C2-symmetric pyrrolidine can be obtained enantiomerically pure (e.e. ≥ 97%) in 15% overall yield starting from a mixture of isomers of 2,5-hexanediol, via a short reaction sequence using (S)-α-methylbenzylamine as a chiral auxiliary. The crystal and molecular structure of (S)-2'-phenyl-N-ethyl-(2S,5S)-dimethylpyrrolidine picrate 5, showing an antiparallel stacking of the picrate units, is also reported.