3-Quinuclidinone → 3-Hydroxyquinuclidine-3-carbonitrile
Reaction equation
[N:1]12CCC(CC1)C(CO)[CH2:2]2.[N:11]12[CH2:18][CH2:17][CH:14]([CH2:15][CH2:16]1)[C:13](=[O:19])[CH2:12]2>>[C:2]([C:13]1([OH:19])[CH:14]2[CH2:17][CH2:18][N:11]([CH2:16][CH2:15]2)[CH2:12]1)#[N:1]Participants
3
Procedure
A process for the preparation of quinuclidine-3-methanol comprising reacting quinuclidine-3-one acid addition salt with an alkali metal cyanide in an aqueous media to obtain 3-cyano-3-hydroxy-quinuclidine, reacting the latter with anhydrous methanol in the presence of hydrogen chloride gas followed by treatment with aqueous alkali to obtain methyl 3-hydroxy-quinuclidine-3-carboxylate, reacting the latter with thionyl chloride to form methyl 1-azabicyclo(2,2,2)oct-2-ene-3-carboxylate, hydrogenating the latter with Raney nickel to obtain methyl 1-azabicyclo(2,2,2)octane-3-carboxylate and reducing the latter to obtain quinuclidine-3-methanol.
Sources & evidence
- ORD record
- ord-957eec28b02c4e7aa8b9f554707df3b4
- Source dataset
- uspto-grants-1990_05
- Patent number
- US04925942
Reaction notes
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