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US 6,388,083 B2Granted
Process for the synthesis of (2S)-phenyl-3-piperidone
AssigneeMerck & Co., Inc.
InventorsJaemoon Lee, David Askin, Thoa Hoang
Life of this patent
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Abstract
The present invention is concerned with novel processes for the preparation of (2S)-phenyl-3-piperidone. This compound is useful as an intermediate in the synthesis of compounds which possess pharmacological activity.
Claims14
A process for the preparation of a compound of the formula:
- which comprises:
- reacting phenylacetylene with an organometallic base followed by 1-bromo-3-chloropropane to give a compound of the formula:
- which compound is reduced under hydrogenation conditions to give a compound of the formula:
- which compound is oxidized to give a compound of the formula:
- which compound is reacted with benzyl amine to give a compound of the formula:
- which compound is reacted with methanesulfonyl chloride in the presence of an amine base followed by reaction with a tetra-alkylammonium acetate to give a compound of the formula:
- which compound is deprotected under hydrogenation conditions followed by reaction with tert-butyloxycarbonyl anhydride to give a compound of the formula:
- which compound is hydrolysed with a base to give a compound of the formula:
- which compound is oxidized under Moffat or Swern conditions to give a compound of the formula:
- which compound is deprotected to give (2S)-phenyl-3-piperidone of the formula:
7 more elements
A process for the preparation of (2S)-phenyl-3-piperidone of the formula:
- which comprises:
- reacting a compound of the formula:
- with methanesulfonyl chloride in the presence of an amine base followed by reaction with a tetra-alkylammonium acetate to give a compound of the formula:
- which compound is deprotected under hydrogenation conditions followed by reaction with tert-butyloxycarbonyl anhydride to give a compound of the formula:
- which compound is hydrolysed with a base to give a compound of the formula:
- which compound is oxidized under Moffat or Swern conditions to give a compound of the formula:
- which compound is deprotected to give (2S)-phenyl-3-piperidone of the formula:
4 more elements
Dependencies are inferred from the claim text.