Fluorous-tethered amine bases for organic and parallel synthesis: Scope and limitations

Tetrahedron Letters

Volumn 43, Issue 36, 2002, Pages 6319-6323

  Lindsley, Craig W ^a   Zhao, Zhijian ^a   Leister, William H ^a   Strauss, Kimberly A ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Amines; Combinatorial chemistry; Fluorous

Indexed keywords

AMINE; BASE; FLUORINE DERIVATIVE; SILICA GEL; SORBENT;

ARTICLE; REACTION ANALYSIS; SOLID PHASE EXTRACTION; SYNTHESIS;

EID: 0037009729     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01399-0     Document Type: Article

References (18)

1. Lindsley C.W., Zhao Z., Leister W.H. Tetrahedron Lett. 43:2002;4225.
2. Lindsley C.W., Zhao Z., Leister W.H., Strauss K.A. Tetrahedron Lett. 43:2002;4467.
3. For related fluorous-tethered scavenger work see: Zhang W., Curran D.P., Chen C.H.-T. Tetrahedron. 58:2002;3871.
4. Ref. 1c For excellent reviews of the area see: (1) Curran, D. P. Synlett 2001, 1488-1496.; (2) Curran, D. P. Pure A Chem. 2000, 72, 1649-1653;
5. Lou Z.Y., Williams J., Read R.W., Curran D.P. J. Org. Chem. 66:2001;4261-4266.
6. FluoroFlash™ columns are available from FTI, Fluorous Technologies Incorporated; www.fluorous.com and Refs. 1 and 2.
7. Compound 1 is commercially available from FTI, cat. no. F017022-0010, $40/g.
8. 2 (M+H), 654.1295; found 654.1294.
9. 7COCl is available from Aldrich Chemical, cat. no. 29,090-4, $2.88/g. The diamines were purchased from Aldrich, Lancaster and TCI.
10. 3O (M+H), 508.0501; found 508.0495.
11. The crude reaction is applied to a 2 g silica transfer column (Part #: 622-0057S) atop a 5 g FluoroFlash™ column (Part #: 801-0058S), pre-washed with aqueous methanol and attached to a multi-port vacuum manifold. Air is drawn through for 2 min, and then 10 mL of a 20% aqueous methanol solution is added and slowly eluted under a -5 psi vacuum and the first 5 mL collected into a test tube.
12. Dandapani S., Curran D.P., Ley S.V., Massi A., Rodriguez F., Harwell D.C., Lewthwaite R.A., Pritchard M.C., Reid A.M., Zhang S.-Q., Fukase K., Izumi M., Fukase Y., Kusumoto S., Bosanac T., Yang J., Wilcox C.S. Chemtracts. 11:2001;635-641.
13. 2O] to 100% (0.05%TFA/MeCN).
14. Replacement of the 2 g silica transfer column (Part #: 622-0057S) atop a 5 g FluoroFlash™ column (Part #: 801-0058S) with a Varian Bond Elut 1 g SCX column (Part #: 12256011) generates the 'mixed sorbent' SPE column. Elution with aqueous methanol under a -5 psi vacuum.
15. All compounds fully characterized by LCMS, NMR and HRMS (accurate mass measurements provide by Chuck W. Ross III).
16. 2O/0.05%TFA), 4 min gradient, >98% pure.
17. 2O/0.05%TFA), 4 min gradient, >98% pure.