Methyl vinyl ketone → HCID 23042277, compound

Participants

Reaction Steps

Other chiral γ-aminoalcohols include cis-2-phenyl-4-hydroxypiperidine (which may be prepared by the Michael addition of O-benzylhydroxylamine to methyl vinyl ketone to yield 2-(benzyloxyamino)ethyl methyl ketone, followed by an intramolecular Mannich reaction with benzaldehyde to yield 1-benzyloxy-4-oxo-2-phenylpiperidine, reduction with sodium borohydride to the corresponding 4-hydroxy compound, removal of the N-benzyloxy group with hydrogen and palladium catalyst, and resolution of the resulting 4-hydroxy-2-phenylpiperidine with the use of an optionally active acid, such as mandelic acid) and the like.

Provenance & Evidence