Synthesis of novel substituted 3,8,11-triazaspiro[5,6]dodecan-7-ones

Tetrahedron Letters

Volumn 52, Issue 8, 2011, Pages 849-852

  Qin, Lan Ying ^a   Cole, Andrew G ^a   Metzger, Axel ^a   Saionz, Kurt W ^a   Henderson, Ian ^a  

^a Ligand Pharmaceuticals Inc   (United States)

Author keywords

Solid phase; Triazaspiro 5,6 dodecan 7 one

Indexed keywords

3,8,11 TRIAZASPIRO[5,6]DODECAN 7 ONE; PIPERIDINE; UNCLASSIFIED DRUG;

ARTICLE; SOLID PHASE SYNTHESIS;

EID: 78751575304     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.150     Document Type: Article

References (13)

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9. 2. Prior to the initiation of a solid-phase reaction the resin is typically washed two times with the reaction solvent.
10. D.A. Rich, and S.K. Gurwara J. Am. Chem. Soc. 97 1975 1575 1579
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12. The Alloc protecting group was removed under the following conditions: a THF solution of 1,3-dimethylbarbituric acid (5.0 equiv) was degassed with argon prior to the addition to the resin. Tetrakis(triphenylphosphine)palladium(0) (0.25 equiv) was then added as a solid and the resulting resin suspension shaken for 18 h at 25 °C.
13. Analytical standards of 17a-f were synthesized using the combined solution-phase and solid-phase approach described in this Letter, and purified by semi-preparative HPLC. Analytical HPLC analysis was conducted using a PDA-linked Waters Millenium 2690 and Phenomenex Luna 3um 50 × 3 mm C8 column.