5-(Pyridin-2-yl)pent-4-yn-1-ol → 5-(2-Piperidyl)-pentan-1-ol
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]#[C:8][CH2:9][CH2:10][CH2:11][OH:12]>[Rh]>[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
5-(2-Pyridyl)-4-pentyn-1-ol, prepared as in Example 41, is reduced by hydrogenating using rhodium on carbon as catalyst to give 5-(2-piperidyl)-pentan-1-ol. Treating that intermediate with methyl iodide and sodium hydride gives the N-methyl compound. Brominating, reacting the bromo compound with t-butyl lithium and 5-trimethylsilyl-3-furaldehyde, then oxidizing by the procedure of Example 41 gives 4-[1-acetoxy-6-(N-methylpiperidyl)hexyl]-5-hydroxy-2(5H)-furanone.
Sources & evidence
- ORD record
- ord-235c5f2be95343ee8acc100f44aa7ea4
- Source dataset
- uspto-grants-1992_07
- Patent number
- US05134128
Reaction notes
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