Solid phase reductive alkylation of secondary amines

Tetrahedron Letters

Volumn 37, Issue 27, 1996, Pages 4819-4822

  Khan, Nawaz M ^a   Arumugam, Vijayalakshmi ^a   Balasubramanian, Shankar ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE;

ALKYLATION; ARTICLE; DRUG PURITY; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030200350     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00945-8     Document Type: Article

References (23)

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20. 2 could be removed after the reaction by washing successively with either aq. alkali metal-bisulphate or aq. citric acid, however, it's buildup inhibits the reaction.
21. 9. High capacity (3.5 meq.) chloromethyl polystyrene (Polymerlabs) was converted to the Wang resin by reaction with 4-hydroxybenzyl alcohol (3 eq.) and sodium methoxide (3 eq.) under argon for 3 days in a shaker/water bath at 50 °C. The proline derivative was formed by shaking the Wang resin with Fmoc-proline (2 eq.) for 15 minutes at room temperature, followed by the successive addition of pyridine (3.3 eq.) and 2,6-dichlorobenzoyl chloride (2 eq.) and stirring overnight under argon at room temperature. Unreacted sites were capped with benzoyl chloride.
22. 10. No reduction of acid functionality was observed when using borane-pyridine complex.
23. 2 and MeOH then dried under vacuum and finally cleaved using 95% TFA.