Bicyclo(2.2.1)heptan-2-one → 2-Methylbicyclo[2.2.1]heptan-2-ol
Reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][C:2]2=[O:8].[CH3:9][Mg]I>>[CH3:9][C:2]1([OH:8])[CH2:3][CH:4]2[CH2:7][CH:1]1[CH2:6][CH2:5]2Participants
Procedure
Norbornanone (I) is reacted with methylmagnesium iodide to give 2-methyl-2-norbornanol (II). The compound (II) is reacted with acetic acid and a 75% solution of sulfuric acid to give 2-acetoxy-1-methylnorbornane (III) which is then converted into 1-methyl- 2-norbornanol (IV) with lithium-aluminum hydride. Then the compound (IV) is enzymatically resolved according to the method reported by Christian Triantaphylides et al., Tetrahedron Letters, 26(15), 1857 (1985) to give (1S)-1-methyl-2-norbornanol (V). This optically active alcohol (V) is then oxidized with pyridine dichromate complex to give (1S)-1-methyl-2-norbornanone (VI). The compound (VI) is reacted with methyltriphenylphosphonium bromide in the presence of n-butyllithium to give (1S)-2-methylenenorbornane (VII) which is then treated with peracetic acid to give an epoxy compound. This epoxy compound is treated with a boron trifluoride etherate complex to give (1S,2S)-1-methyl-2-norbornyl aldehyde (VIII) which is then reduced with lithium aluminum hydride to give (1S,2S)-1-methyl-2-hydroxymethylnorbornane (IX).
Sources & evidence
- ORD record
- ord-b2b07d69303f480eaf94245cff1939e3
- Source dataset
- uspto-grants-1995_10
- Patent number
- US05463118
Reaction notes
Loading…