Processes and intermediates for resolving piperidyl acetamide stereoisomers

• US 7,459,560 B2
• Filed: 02/23/2006
• Issued: 12/02/2008
• Est. Priority Date: 05/22/1997
• Status: Expired due to Fees

• Current Assignee: Celgene Corporation (Bristol-Myers Squibb Company)
• Original Assignee: Celgene Corporation (Bristol-Myers Squibb Company)
• Inventors: Khetani, Vikram, Ramaswamy, Sowmianarayanan, Luo, Yalin
• Primary Examiner(s): Andres; Janet L.
• Assistant Examiner(s): Gallis; David E
• Application Number:
  US11/360,877
• Publication Number:
  US 20060142583A1
• Time in Patent Office: 1,013 Days
• Field of Search: 546/229, 546/190, 546/233
• US Class Current: 546/233
• CPC Class Codes: C07D 211/34 with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Abstract

Processes and intermediates for preparing 2-substituted piperidines such as 2-substituted d-threo piperidines are provided, including processes and intermediates for resolution of piperidyl acetamide stereoisomers.

Claims

1. A synthetic process comprising the steps of:

providing a mixture of said d,l-threo piperidyl acetamide stereoisomers having formulas;

2. The process of claim 1 wherein R₁ is phenyl.

3. The process of claim 1 wherein said solvent is an alkyl alcohol having 1 to about 5 carbon atoms.

4. The process of claim 3 wherein said alkyl alcohol is isopropanol.

5. The process of claim 1, wherein said physically isolated acid salts are d-threo acid salts, said process further comprising reacting said d-threo acid salts with aqueous base to form said d-threo piperidine acetamide.

6. The process of claim 5 further comprising reacting said d-threo piperidine acetamide with an alcohol having 1 to about 5 carbon atoms in the presence of acid to form a d-threo piperidine acetate.

7. The process of claim 1 wherein said d,l-threo piperidyl acetamide stereoisomers are prepared by reacting a pyridine having formula:

8. The product of the process of claim 1.