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Tetrahedron Letters
Volumn 33, Issue 40, 1992, Pages 5895-5896
Alkylation of the cyclic sulfamate of prolinol. Preparation of optically active 2-alkyl-substituted pyrrolidines
Author keywords

[No Author keywords available]
Indexed keywords

PYRROLIDINE DERIVATIVE;
EID: 0026475477     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)61082-1     Document Type: Article
Times cited : (24)
References (10)
  • 5
    • 84918223433 scopus 로고    scopus 로고
    • 3S) and a 2M+Li peak at m/e 487 in its negative ion mass spectrum.
  • 6
    • 84918223432 scopus 로고    scopus 로고
    • 4OH.
  • 7
    • 84918223431 scopus 로고    scopus 로고
    • 2 at −70° was added 2.26 ml 1.63M n-butyllithium in hexane (3.68 mmole) over 40 min. After wash in of the base with 1.5 ml dry THF the white slurry was stirred at −70° for 1 hr. Cyclic sulfamate 1 (0.5 g, 3.06 mmole) dissolved in 2.0 ml dry THF was added over 8 min. The mixture was allowed to warm to room temperature and stir overnight. The solvent was evaporated at 40° to give a beige foam which was refluxed overnight in 6 ml of 2N hydrochloric acid (an equivalent volume of ethanol was added in the case of the less soluble salts 2b and 2c). The reflux condenser was replaced with a short-path distillation head to allow removal of veratrole by steam distillation. Water was added to make up for the distillate and the mixture stirred while cooling. The resulting precipitate (mostly bi-vetatrole) was filtered and the aqueous phase [[Truncated]]

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