138713-63-0

Basic information

• Product Name: (1R,9aR)-Octahydro-1-hydroxymethyl-1-<(S)-(4-methylphenyl)sulfinyl>-2H-quinolizine
• Synonyms: (1R,9aR)-Octahydro-1-hydroxymethyl-1-<(S)-(4-methylphenyl)sulfinyl>-2H-quinolizine
• CAS NO: 138713-63-0
• Molecular Weight: 307.457
• Mol File: 138713-63-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1R,9aR)-Octahydro-1-hydroxymethyl-1-<(S)-(4-methylphenyl)sulfinyl>-2H-quinolizine(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,9aR)-Octahydro-1-hydroxymethyl-1-<(S)-(4-methylphenyl)sulfinyl>-2H-quinolizine(138713-63-0)
• EPA Substance Registry System: (1R,9aR)-Octahydro-1-hydroxymethyl-1-<(S)-(4-methylphenyl)sulfinyl>-2H-quinolizine(138713-63-0)

Safety Data

• Hazardous Substances Data: 138713-63-0(Hazardous Substances Data)

Upstream product

• 138713-58-3 (1R,9aR)-Octahydro-1-<(R)-(4-methylphenyl)sulfinyl>-2H-quinolizine 
• 138732-27-1 (1S,9aR)-Octahydro-1-<(R)-(4-methylphenyl)sulfinyl>-2H-quinolizine 
• 138713-57-2 3,4,6,7,8,9-Hexahydro-1-<(R)-(4-methylphenyl)sulfinyl>-2H-quinolizine 
• 138713-56-1 (+)-2,3,4,5-Tetrahydro-6-<(R)-(4-methylphenyl)sulfinylmethyl>pyridine 
• 1517-82-4 (-)-menthyl p-toluenesulfinate 
• 1462-92-6 6-methyl-2,3,4,5-tetrahydro-pyridine 
• 138713-61-8 Ethyl (1R,9aR)-Octahydro-1-<(S)-(4-methylphenyl)sulfinyl>-2H-quinolizine-1-carboxylate 
• 138713-59-4 (1R,9aS)-Octahydro-1-<(R)-(4-methylphenyl)sulfinyl>-2H-quinolizine 
• 138713-60-7 (1S,9aS)-Octahydro-1-<(R)-(4-methylphenyl)sulfinyl>-2H-quinolizine 
• 138713-66-3 Ethyl (1R,9aS)-Octahydro-1-<(S)-(4-methylphenyl)sulfinyl>-2H-quinolizine-1-carboxylate 
• 138713-65-2 Ethyl (1S,9aS)-Octahydro-1-<(S)-(4-methylphenyl)sulfinyl>-2H-quinolizine-1-carboxylate 

Downstream Products

• 486-71-5 (+)-epilupinine 

Relevant articles and documents

Asymmetric total synthesis of (-)-lupinine and (+)-epilupinine via α-sulfinyl ketimine. Stereocontrolled reduction of β-sulfinyl enamines

(-)-Lupinine and (+)-epilupinine [(1R,9aR)- and (1S,9aR)-octahydro-1-hydroxymethyl-2H-quinolizine] were synthesized from (+)-2,3,4,5-tetrahydro-6-[(R)-(4-methylphenyl)sulfinylmethyl]pyridine (4) in five steps. The intermediate, 3,4,6,7,8,9-hexahydro-1-[(R)-(4-methylphenyl)sulfinyl]-2H-quinolizine (7), was stereoselectively reduced with cerium(III) chloride heptahydrate and sodium borohydride to give predominantly C-9a-R isomers, (9aR)-octahydro-1-[(R)-(4-methylphenyl)sulfinyl]-2H-quinolizines.