Remarkable switch of regioselectivity in epoxide ring opening of 3-benzyl-7-oxa-3-azabicyclo[4.1.0]heptane with amines: practical synthesis of trans-4-amino-3-hydroxypiperidines and trans-3-amino-4-hydroxypiperidines

Tetrahedron Letters

Volumn 51, Issue 21, 2010, Pages 2832-2834

  Tokuda, Osamu ^a   Aikawa, Toshiaki ^a   Ikemoto, Tetsuya ^a   Kurimoto, Isao ^a  

^a SUMITOMO CHEMICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 AMINO 4 HYDROXYPIPERIDINE DERIVATIVE; 3 BENZYL 7 OXA 3 AZABICYCLO[4.1.0]HEPTANE; 3,4 EPOXYPIPERIDINE DERIVATIVE; 4 AMINO 3 HYDROXYPIPERIDINE DERIVATIVE; NUCLEOPHILE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTRON TRANSPORT; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 77950940478     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.03.061     Document Type: Article

References (21)

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11. The synthesis of epoxide 3: see Ref. 2f and. Grishina G.V., Borisenko A.A., Veselov I.S., and Petrenko A.M. Russ. J. Org. Chem. 41 (2005) 272
12. Naito T., Nakagawa K., Nakamura T., Kasei A., Ninomiya I., and Kiguchi T. J. Org. Chem. 64 (1999) 2003
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14. The regioselective synthesis of trans-3-amino-4-substituted piperidines has been reported:. Hu X.E., Kim N.K., Ledoussal B., and Colson A.-O. Tetrahedron Lett. 43 (2002) 4289
15. Hu X.E. Tetrahedron Lett. 43 (2002) 5315
16. 4 and evaporated to provide desired adduct. The residue was purified by flash chromatography on silica gel to give the corresponding adduct.
17. 3OD) δ 140.7, 138.6, 130.4, 129.5, 129.3, 129.2, 128.3, 128.1, 71.5, 63.5, 62.1, 60.2, 53.0, 51.6, 29.5 ppm.
18. 2NH has been reported as only one example for highly C3 selective epoxide ring-opening reaction. However, the yield of product was low (27%) in their case: see Ref. 3.
19. 4 and evaporated to provide desired adduct. If necessary, the residue was purified by flash chromatography on silica gel to give the corresponding adduct.
20. 3OD) δ 140.5, 138.6, 130.5, 129.45, 129.35, 129.2, 128.3, 128.1, 72.9, 63.5, 61.0, 56.4, 52.8, 52.0, 33.8 ppm.
21. Chini M., Crotti P., Gardelli C., and Macchia F. Tetrahedron 50 (1994) 1261 and references cited therein