A concise synthesis of N-(trideuteromethyl)morpholine-N-oxide monohydrate

Synlett

Volumn , Issue 12, 1999, Pages 1972-1974

  Rosenau, Thomas ^a   Potthast, Antje ^a   Kosma, Paul ^a  

^a UNIVERSITY OF NATURAL RESOURCES AND LIFE SCIENCES   (Austria)

Author keywords

Amine oxides; N methylmorpholine N oxide; Sodium percarbonate; Toc protecting group

Indexed keywords

MORPHOLINE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0032732497     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2963     Document Type: Article

References (19)

1. 4: Schroder, M. Chem. Rev. 1980, 80, 187. Jacobsen, E.N.; Markò, I.; Mungall, W.S.; Schröder, G.; Sharpless, K.B. J. Am. Chem. Soc. 1988, 110, 1968.
2. 4: Schroder, M. Chem. Rev. 1980, 80, 187. Jacobsen, E.N.; Markò, I.; Mungall, W.S.; Schröder, G.; Sharpless, K.B. J. Am. Chem. Soc. 1988, 110, 1968.
3. 4: Schroder, M. Chem. Rev. 1980, 80, 187. Jacobsen, E.N.; Markò, I.; Mungall, W.S.; Schröder, G.; Sharpless, K.B. J. Am. Chem. Soc. 1988, 110, 1968.
4. 4: Schroder, M. Chem. Rev. 1980, 80, 187. Jacobsen, E.N.; Markò, I.; Mungall, W.S.; Schröder, G.; Sharpless, K.B. J. Am. Chem. Soc. 1988, 110, 1968.
5. a) Chanzy, H. J. Polym, Sci. Polymer Phys. Ed. 1980, 1137.
6. b) Taeger, E.; Michels, C.; Nechtawal, A. Papier 1991, 12, 784.
7. Rosenau, T.; Potthast, A.; Kosma, P.; Chen, C.L.; Gratzl, J.S. J. Org. Chem. 1999, 64, 2166.
8. Buijtenhuis, F.A.; Abbas, M.; Witteveen, A.J. Papier 1986, 40, 615.
9. Representative procedures for the preparation of amine oxides by oxidation of tertiary amines with aqueous hydrogen peroxide of different concentrations: Hoh, G.L.H.; Barlow, D.O.; Chadwick, A.F.; Lake, D.B.; Sheeran, S.R. J. Am. Oil Chem. Soc. 1963, 9, 268. Huisgen, R.; Bayerlein, F.; Heydkamp, W. Chem. Ber. 1959, 92, 3223; besides vast patent literature.
10. Representative procedures for the preparation of amine oxides by oxidation of tertiary amines with aqueous hydrogen peroxide of different concentrations: Hoh, G.L.H.; Barlow, D.O.; Chadwick, A.F.; Lake, D.B.; Sheeran, S.R. J. Am. Oil Chem. Soc. 1963, 9, 268. Huisgen, R.; Bayerlein, F.; Heydkamp, W. Chem. Ber. 1959, 92, 3223; besides vast patent literature.
11. Preparation of anhydrous or lower-hydrate amine-oxides from aqueous solutions or higher hydrates: Köster, R; Morita, Y. Liebigs Ann. Chem. 1967, 704, 70. Sonderquist, J.A.; Anderson, C.L. Tetrahedron Lett. 1986, 27, 3961.
12. Preparation of anhydrous or lower-hydrate amine-oxides from aqueous solutions or higher hydrates: Köster, R; Morita, Y. Liebigs Ann. Chem. 1967, 704, 70. Sonderquist, J.A.; Anderson, C.L. Tetrahedron Lett. 1986, 27, 3961.
13. For the preparation of Toc-Br see: Rosenau, T.; Habicher, W.D. Tetrahedron 1995, 51, 7919. Protection of amines with Toc-Br and removal of the protecting group: Rosenau, T.; Chen, C.L.; Habicher, W.D. J. Org. Chem. 1995, 60, 8120.
14. For the preparation of Toc-Br see: Rosenau, T.; Habicher, W.D. Tetrahedron 1995, 51, 7919. Protection of amines with Toc-Br and removal of the protecting group: Rosenau, T.; Chen, C.L.; Habicher, W.D. J. Org. Chem. 1995, 60, 8120.
15. 2 adduct, have not been tested.
16. The melting point is also a good indicator of the water content, cf.: m.p. = 74-76 °C: Eastman Kodak Co., Patent GB 1144048, 1966; Chem. Abstr. 1969, 70, 106537r. m.p. = 75 °C: Krafft, M.E.; Cheung, Y.Y.; Wright, C.; Cali, R. J. Org. Chem. 1996, 61, 3912.
17. The melting point is also a good indicator of the water content, cf.: m.p. = 74-76 °C: Eastman Kodak Co., Patent GB 1144048, 1966; Chem. Abstr. 1969, 70, 106537r. m.p. = 75 °C: Krafft, M.E.; Cheung, Y.Y.; Wright, C.; Cali, R. J. Org. Chem. 1996, 61, 3912.
18. The melting point is also a good indicator of the water content, cf.: m.p. = 74-76 °C: Eastman Kodak Co., Patent GB 1144048, 1966; Chem. Abstr. 1969, 70, 106537r. m.p. = 75 °C: Krafft, M.E.; Cheung, Y.Y.; Wright, C.; Cali, R. J. Org. Chem. 1996, 61, 3912.
19. 2:120.0975 (Δ = 0.0005 amu).