Reaction of Trimethylsilyl Benzhydryl Ethers with Methyl N-(Trimethylsilyl)pyroglutamate: An Easy and Rapid N-Alkylation

Synlett

Volumn 1997, Issue 8, 1997, Pages 998-1000

  Rigo, Benoît ^a   Gautret, Philippe ^a   Legrand, Anne ^a   Hénichart, Jean Pierre ^b   Couturier, Daniel ^c  

^a Ecole des Hautes Etudes d'Ingenieur   (France)

^b 59006   (France)

^c UNIV LILLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003074513     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-944     Document Type: Article

References (20)

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4. Liénard, P. ; Royer, J. ; Quirion, J.-C. ; Husson, H.-P. Tetrahedron Lett. 1991, 32, 2489. Liénard, P.; Quirion, J.-C.; Husson, H.-P. Tetrahedron 1993, 49, 3995.
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7. This will be described in a next publication.
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14. The reaction of benzyl halides with N-(trimethylsilyl) pyrrolidinone, catalyzed by trimethylsilyl triflate has already been described: Kramarova, E. P. ; Shipov, A. G. ; Orlova, N. A. ; Artamkina, O. B. ; Belavin, I. Yu. ; Baukov, Yu. J. Gen. Chem USSR. 1988, 970.
15. 2).
16. This chloride was prepared in 40% yield by treatment of the corresponding benzhydryl silyl ether with a concentrated hydrogen chloride solution at 0°C during 30 min.
17. Mitsunobu, O. ; Wada , M. ; Sano, T. J. Am. Chem. Soc. 1972, 94, 679.
18. Gautret, P. ; El Ghammarti, S. ; Legrand, A. ; Couturier, D. ; Rigo, B. Synth. Commun. 1996, 26, 707.
19. 2).
20. We have checked that an equimolar mixture of N-silyl ester 7 and triflic acid or of methyl pyroglutamate 11 and trimethylsilyl triflate gave the same NMR spectra, and that heating such a mixture in vacuo allows the distillation of methyl pyroglutamate 11 and trimethylsilyl triflate.