189498-44-0

Basic information

• Product Name: (S)-3-((3R,4S)-1-benzyl-4-phenyl-pyrrolidine-3-carbonyl)-4-phenyl-oxazolidin-2-one
• Synonyms: (S)-3-((3R,4S)-1-benzyl-4-phenyl-pyrrolidine-3-carbonyl)-4-phenyl-oxazolidin-2-one
• CAS NO: 189498-44-0
• Molecular Weight: 426.515
• Mol File: 189498-44-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-3-((3R,4S)-1-benzyl-4-phenyl-pyrrolidine-3-carbonyl)-4-phenyl-oxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-((3R,4S)-1-benzyl-4-phenyl-pyrrolidine-3-carbonyl)-4-phenyl-oxazolidin-2-one(189498-44-0)
• EPA Substance Registry System: (S)-3-((3R,4S)-1-benzyl-4-phenyl-pyrrolidine-3-carbonyl)-4-phenyl-oxazolidin-2-one(189498-44-0)

Safety Data

• Hazardous Substances Data: 189498-44-0(Hazardous Substances Data)

Upstream product

• 93102-05-7 N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine 
• 141209-95-2 (4S)-4-phenyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one 

Downstream Products

• 221141-87-3 [(3R,4S)-1-benzyl-4-phenylpyrrolidin-3-yl]methanol 

Relevant articles and documents

A practical and efficient synthesis of (3R,4S)-1-benzyl-4- phenylpyrrolidine-3- carboxylic acid via an aziridinium ion intermediate

A practical and efficient synthesis of (3R,4S)-1-benzyl4-phenylpyr- rolidine-3-carboxylic acid (1), a key chiral building block for synthesis of biologically active compounds was established by utilizing a stereospecific and regioselective chlorination of in situ generated aziridinium ion, followed by a nitrile anion cyclization. Starting from commercially available (R)-styrene oxide and 3-(benzylamino)propionitrile, the four-step synthesis features a through process without purification of intermediates until isolation of crystalline 1. The robust, chromatography-free and reproducible synthesis of 1 achieved an 84% overall yield from (R)-styrene oxide. This highly efficient process was successfully demonstrated at pilot scale with 17 kg output of 1.

SPIRO COMPOUNDS AND METHODS FOR THE MODULATION OF CHEMOKINE RECEPTOR ACTIVITY

Compounds of formula I insert formula I from claim 1 wherein X, Y, Z, W, R1 and R2 as defined herein, or pharmaceutically acceptable salts, hydrates or solvates thereof, are useful for the modulation of CCR5 chemokine receptor activity.