Selective benzoylation of primary amines in the presence of secondary amines
β Scribed by Tao Wang; Zhongxing Zhang; Nicholas A. Meanwell
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 120 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Compounds containing both primary and secondary amine moieties in the same molecule were treated sequentially with two equivalents of n-butyllithium at room temperature, two equivalents of TMSCI, one equivalent of nbutyllithium and one equivalent of benzoyl chloride, to afford mono-benzoylated diamines. Under these conditions, the primary amine moiety was selectively benzoylated.
π SIMILAR VOLUMES
Many primary amines when heated with a catalytic amount of a strong base are converted into secondary amines. Sodium hydride (0.2-0.3 mole per mole of amine) CH3(CH2)4CH2NH2 90-110~ 16 hr
Secondary amides activated with a Cbz group can be reduced to their corresponding hemiaminals using lithium borohydride. Hydrogenation then removes the Cbz and hydroxyl groups to produce the related amine. Tertiary amides are not affected.
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