Oxidative deprotection of diphenylmethylamines

Organic Letters

Volumn 1, Issue 9, 1999, Pages 1395-1397

  Sampson, Peter B ^a   Honek, John F ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000372979     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990956i     Document Type: Article

References (18)

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16. N-Diphenylmethylamines 1a-1e were prepared by reductive amination of diphenylmethylamine and an aldehyde in the presence of sodium cyanoborohydride. The norleucine analogue 1f was prepared by transamination of norleucine methyl ester with benzophenone imine followed by reduction with sodium cyanoborohydride.
17. To an anhydrous solution of benzene (3 mL) and crushed 4A molecular sieves under an argon atmosphere were added the Dpm-amine (1 mmol) and DDQ (1 mmol). The reaction mixture was heated to 60°C for 1 h in the absence of light. The deep red solution became light orange over the course of the reaction with concomitant production of a purple precipitate. The solution was cooled to room temperature and quickly filtered through a small column charged with Brockmann 1 basic alumina and washed with toluene. The solvents were removed in vacuo. The resulting yellow oils were dissolved into diethyl ether (10 mL) and 0.1 N HCl (10 mL). The two-phase mixture was vigorously stirred for 4-6 h. The phases were separated, and the ether layer was washed with 0.1 N HCl (2 × 5 mL). The aqueous layers were combined and washed with diethyl ether (2 × 5 mL). Concentration of the aqueous fraction gave the hydrochloride salts of the desired amines.
18. Gallagher, M. J.; Hoegger, H.; Aust. J. Chem. 1980, 33, 287-94.