1239015-87-2

Upstream product

• 91-22-5 quinoline 
• 139149-49-8 (S)-4-benzyloxazolidin-2-one-3-carbonyl chloride 

Downstream Products

• 1239015-89-4 (S)-4-benzyl-3-[(1aS,7bR)-1a,2,3,7b-tetrahydrooxireno[2,3-c]quinoline-3-carbonyl]oxazolidine-2-one 
• 1239015-88-3 (S)-4-benzyl-3-[(1aR,7bS)-1a,2,3,7b-tetrahydrooxireno[2,3-c]quinoline-3-carbonyl]oxazolidine-2-one 
• 132875-37-7 (5R)-5-amino-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-1(2H)-one 
• 1239015-91-8 methyl (3S)-3-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate 
• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 

Relevant academic research and scientific papers

A new synthesis of (R)-(-)-sumanirole (PNU-95666E)

A twelve-step synthesis of (R)-(-)-sumanirole hydrochloride, starting from quinoline, has been achieved. The key reaction features selective epoxidation of the C3-C4 double bond of a 1,2-dihydroquinoline bearing a chiral auxiliary at N-1.

Remote control of the C-3-C-4 double-bond epoxidation of a chiral 1,2-dihydroquinoline: Application to the synthesis of (-)-(r)-sumanirole (PNU-95666E)

A twelve-step synthesis of (-)-(R)-sumanirole starting from quinoline is described. The first synthetic approach, using a chiral Reissert adduct, was too problematic to be pursued further. In the second successful approach, the authors took advantage of the stereoselective epoxidation of a 1,2-dihydroquinoline bearing an Evans' chiral auxiliary at N-1. A twelve-step synthesis of (-)-(R)-sumanirole hydrochloride has been developed from quinoline. In the successful approach, the key reaction is a diastereoselective epoxidation of the C-3-C-4 double bond of a 1,2-dihydroquinoline bearing a chiral oxazolidinone-derived auxiliary at N-1.