Methyl vinyl ketone → HCID 23042277, compound
Reaction equation
C1([C@H]2[CH2:12][C@@H:11]([OH:13])[CH2:10][CH2:9]N2)C=CC=CC=1.[CH2:14]([O:21][NH2:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(C(C)=O)=C>>[CH3:12][C:11]([CH2:10][CH2:9][NH:22][O:21][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:13]Participants
4
Procedure
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.
Sources & evidence
- ORD record
- ord-2913478a7e684832a6898a7d58ce3440
- Source dataset
- uspto-grants-1990_07
- Patent number
- US04943635
Reaction notes
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