(-)-2-Cyano-6-phenyloxazolopiperidine TCI C1363

Chemical Identity

Other names: (-)-5-Cyano-3-phenyl-2,3,5,6,7,8-hexahydro-5H-oxazolo[3,2-a]pyridine · (-)-2,3,5,6,7,8-Hexahydro-3-phenyl-5H-oxazolo[3,2-a]pyridine-5-carbonitrile
CAS No.: 88056-92-2
Formula: C14H16N2O
Molecular weight: 228.30 g/mol
Purity: >98.0%(HPLC)(T)

Full identifiers (IUPAC, SMILES, InChIKey)

IUPAC: (3R,5S,8aR)-3-phenyl-3,5,6,7,8,8a-hexahydro-2H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile
SMILES: C1CC(N2C(C1)OCC2C3=CC=CC=C3)C#N
InChIKey: GQHMNZGZXHZLEN-MELADBBJSA-N
MDL: MDL00142338
PubChem: CID 2724819

Rp 6.070.050,00

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TCI C1363 (-)-2-Cyano-6-phenyloxazolopiperidine (CAS 88056-92-2) is a bicyclic chiral synthon designed for the asymmetric synthesis of piperidine alkaloids. Its alpha-aminonitrile function is remarkably versatile: deprotonation generates a stabilised carbanion for reaction with electrophiles, while loss of cyanide delivers an iminium ion that reacts with nucleophiles. The chiral oxazolidine framework controls the facial approach of incoming reagents, giving substituted piperidines with high diastereoselectivity before the auxiliary is removed. AMI Scientific supplies this TCI chiral building block in a 1 g pack size for asymmetric synthesis research.

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