31608-17-0

Basic information

• Product Name: (S)-(+)-coniine (R)-(-)-mandelic acid salt
• CAS NO: 31608-17-0
• Molecular Weight: 279.379
• Mol File: 31608-17-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-(+)-coniine (R)-(-)-mandelic acid salt(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-coniine (R)-(-)-mandelic acid salt(31608-17-0)
• EPA Substance Registry System: (S)-(+)-coniine (R)-(-)-mandelic acid salt(31608-17-0)

Safety Data

• Hazardous Substances Data: 31608-17-0(Hazardous Substances Data)

Upstream product

• 611-71-2 (R)-Mandelic Acid 
• 458-88-8 coniine 

Relevant articles and documents

Modified fry cyanation of a chiral pyridinium salt: Asymmetric syntheses of (-)-coniine and (-)-solenopsin A

The synthesis of chiral 2-cyano-Δ4-tetrahydropyridine 5 was carried out in 85 % yield through a modified two-step Fry reductive cyanation of pyridinium salt (+)-3c that used lithium triethylborohydride as the hydride donor. An alkylation-reduction sequence provided 2-alkyl-substituted tetrahydropyridines (+)-10a and (+)-10b in 72-75 % yield after chromatographic purification. This protocol has been applied to the asymmetric syntheses of piperidine alkaloids (-)-coniine and (-)-solenopsin A. The two-step reductive cyanation of chiral pyridinium salt (+)-3c afforded α-amino nitrile 5 in 85 % yield, which underwent an alkylation-reduction sequence followed by removal of the chiral moiety to yield the hemlock alkaloid (-)-coniine as its mandelate salt (>99:1 er). This reaction sequence was also used for the synthesis of the trans-2,6-disubstituted piperidine alkaloid (-)-solenopsin A. Copyright