860640-21-7

Basic information

• Product Name: (R)-1-((S)-2-methyl-propane-2-sulfinyl)-2-phenyl-pyrrolidine
• Synonyms: (R)-1-((S)-2-methyl-propane-2-sulfinyl)-2-phenyl-pyrrolidine
• CAS NO: 860640-21-7
• Molecular Weight: 251.393
• Mol File: 860640-21-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (R)-1-((S)-2-methyl-propane-2-sulfinyl)-2-phenyl-pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-((S)-2-methyl-propane-2-sulfinyl)-2-phenyl-pyrrolidine(860640-21-7)
• EPA Substance Registry System: (R)-1-((S)-2-methyl-propane-2-sulfinyl)-2-phenyl-pyrrolidine(860640-21-7)

Safety Data

• Hazardous Substances Data: 860640-21-7(Hazardous Substances Data)

Upstream product

• 1089728-89-1 C₁₄H₂₀ClNOS 
• 1218989-24-2 (S,E)-N-(4-chloro-1-phenylbutylidene)-2-methylpropane-2-sulfinamide 
• 186249-76-3 (R,E)-2-methyl-N-(phenylmethylene)-2-propanesulfinamide 
• 860640-13-7 2-Methyl-propane-2-sulfinic acid ((R)-3-[1,3]dioxan-2-yl-1-phenyl-propyl)-amide 
• 31562-43-3 tert-butylsulfinyl chloride 
• 56523-47-8 (R)-2-phenylpyrrolidine 

Downstream Products

• 700-91-4 2-phenyl-1-pyrroline 
• 860640-20-6 (R)-1-((R)-2-methyl-propane-2-sulfinyl)-2-phenyl-pyrrolidine 
• 56523-47-8 (R)-2-phenylpyrrolidine 

Relevant articles and documents

PROCESS FOR SYNTHESIS OF 2-SUBSTITUTED PYRROLIDINES AND PIPERADINES

The present invention provides a highly efficient, versatile one-step process for asymmetric synthesis of either diastereomer of 2-substituted pyrrolidines from a single starting material with excellent yields and high diastereoselectivety. Also provided is a method for the asymmetric synthesis of both diastereomers of 2-substituted piperidines with good yields and excellent diastereoselectivety. Diasteroselectivity is controlled effectively by choice of reducing agent.

A facile asymmetric synthesis of either enantiomer of 2-substituted pyrrolidines

Chemical Reaction Reprentation A new and general method for asymmetric synthesis of either enantiomer of 2-substituted pyrrolidines from a single starting material is described. Reductive cyclization of (Ss)-γ-chloro-N- tertbutanesulfinyl ketimines with LiBHEt3 in THF at -78 to 23 °C afforded (Ss,R)-N-tert-buta.nemnnyl-2-substituted pyrrolidines in excellent yields (88-98%) and with high diastereoselectivity (99:1). The diastereoselectivity is controlled effectively by the choice of reducing agent. Thus, the corresponding epimers of (3 to DIBAL-H/LiHMDS. Deprotection of N-fe/ f-butanesulfinyl-2-substituted pyrrolidines using 4 N HCl in dioxane and MeOH gave the corresponding enantiomers of 2-substituted pyrrolidines in quantative yield. This method was found to be effective for a variety of substrates including aromatic, heteroaromatic, and aliphatic substituents. Extension of this methodology to the formation of 2-substituted piperidines is also illustrated. Reductive cyclization of (5s)-3 in THF at -78 to 23 °C or DIBAL-H/LiHMDS in toluene at -78 to 0 °C afforded the (Ss,R?)-N-tert-butanesulfinyl-2-substituted piperidines in excellent yield (98%) and with high diastereoselectivity (99:1) or (Ss,S)-.N-tert-butanesulfmyl- 2substituted piperidines in good yield (98%) and with high diastereoselectivity (1:99), respectively.