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Concise Synthesis of (2S,3R)-3-Hydroxy-2-phenylpiperidine: An Advanced Key Intermediate of Human Non-Peptide NK-1 Receptor Antagonists
| Content Provider | Scilit |
|---|---|
| Author | Ferreira, Franck Chemla, Fabrice Hélal, Benoît Botuha, Candice Pérez-Luna, Alejandro |
| Copyright Year | 2009 |
| Description | The rapid, high-yielding synthesis of (2S,3R)-3-hydroxy-2-phenylpiperidine, a known advanced key intermediate of some non-peptide human NK-1 receptor antagonists such as (+)-CP-99,994, (+)-CP-122,721 and (+)-LP-733,060, is reported. This synthesis involves the stereoselective addition of racemic 3-(methoxymethoxy)allenylzinc bromide to enantiopure (R$ _{S}$,E)-N-2-benzylidene-2-methylpropane-2-sulfinamide and a ring-closing metathesis reaction as the key steps. Following this procedure, (2S,3R)-3-hydroxy-2-phenylpiperidine is obtained in seven steps in 56.2% overall yield. |
| Related Links | http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0029-1218308.pdf |
| Ending Page | 3118 |
| Page Count | 4 |
| Starting Page | 3115 |
| ISSN | 09365214 |
| e-ISSN | 14372096 |
| DOI | 10.1055/s-0029-1218308 |
| Journal | Synlett |
| Issue Number | 19 |
| Volume Number | 2009 |
| Language | English |
| Publisher | Georg Thieme Verlag KG |
| Publisher Date | 2009-10-23 |
| Access Restriction | Open |
| Subject Keyword | Organic Chemistry Stereoselective Synthesis |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry |
