1189155-63-2

Basic information

• Product Name: (R)-2-(4-BROMOPHENYL)PYRROLIDINE
• Synonyms: (R)-2-(4-BROMOPHENYL)PYRROLIDINE;(2R)-2-(4-broMophenyl)pyrrolidine;(2R)-2-(4-BROMOPHENYL)PYRROLIDINE HCl;Pyrrolidine, 2-(4-bromophenyl)-, (2R)-
• CAS NO: 1189155-63-2
• Molecular Formula: C₁₀H₁₂BrN
• Molecular Weight: 226.11
• Mol File: 1189155-63-2.mol

Chemical Properties

• Boiling Point: 287℃
• Flash Point: 128℃
• Appearance: /
• Density: 1.369
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: (R)-2-(4-BROMOPHENYL)PYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-(4-BROMOPHENYL)PYRROLIDINE(1189155-63-2)
• EPA Substance Registry System: (R)-2-(4-BROMOPHENYL)PYRROLIDINE(1189155-63-2)

Safety Data

• Hazardous Substances Data: 1189155-63-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
(R)-2-(4-BROMOPHENYL)PYRROLIDINE is used as a key intermediate in the synthesis of certain drugs and compounds for medicinal purposes. Its unique structure and properties contribute to the development of new therapeutic agents.
Used in Scientific Research:
(R)-2-(4-BROMOPHENYL)PYRROLIDINE is used as a research chemical to study its properties and potential applications in various fields, including chemistry, biology, and medicine. This helps in understanding its behavior and interactions with other compounds, which can lead to the discovery of new applications and uses.
Used in Drug Synthesis:
(R)-2-(4-BROMOPHENYL)PYRROLIDINE is used as a building block in the synthesis of pharmaceutical compounds. Its presence in the molecular structure can influence the drug's efficacy, potency, and other pharmacological properties, making it an essential component in the development of new medications.

Upstream product

• 1218989-40-2 (R)-1-((S)-2-methyl-propane-2-sulfinyl)-2-(4-bromophenyl)-pyrrolidine 
• 1207729-74-5 (R)-1-((R)-2-methyl-propane-2-sulfinyl)-2-(4-bromophenyl)-pyrrolidine 
• 4559-96-0 1-(4-bromophenyl)-4-chlorobutan-1-one 
• 1218989-39-9 C₁₄H₂₁BrClNOS 
• 1218989-23-1 (S,E)-N-(4-chloro-1-(4-bromophenyl)butylidene)-2-methylpropane-2-sulfinamide 
• 1207455-72-8 tert-butyl (4-(4-bromophenyl)-4-oxobutyl)carbamate 
• 106-37-6 1.4-dibromobenzene 

Relevant articles and documents

Enantioselective Direct Synthesis of Free Cyclic Amines via Intramolecular Reductive Amination

Chiral cyclic amines can be prepared via intramolecular reductive amination of N-Boc-protected amino ketones in a one-pot process. With the complex of iridium and f-spiroPhos as the catalyst, a range of N-Boc-protected amino ketones are smoothly transformed into chiral cyclic free amines in high yields and excellent enantioselectivities (up to 97% ee). Moreover, this method can also be successfully applied to the synthesis of a κ-opioid receptor selective antagonist, (S)-1.

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.

Asymmetric synthesis of 2-substituted pyrrolidines by addition of Grignard reagents to γ-chlorinated N-tert-butanesulfinyl imine

A highly diastereoselective addition of various Grignard reagents to chiral γ-chlorinated N-tert-butanesulfinyl imine resulting in the formation of 2-substituted pyrrolidines is reported. This method is general and also efficient for the preparation of both enantiomers of 2-aryl, 2-alkyl and 2-vinyl substituted pyrrolidines in high yields.