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Creators/Authors contains: "Manoury, Eric"

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  1. ; ; ; ; ; ; (, ChemistrySelect)
    Abstract Simple synthetic routes to regioselectively deuterated tris[2‐(dimethylamino)ethyl]amine (Me6TREN) variants are described. Imine formation with formaldehyde‐d2from tris(2‐aminoethyl)amine (TREN) and subsequent reductions with NaBD4afforded N[CH2CH2N(CD3)2]3ord18‐Me6TREN in 79 % yield. A trisubstitution protocol from 2‐bromo‐N,N‐dimethylacetamide and ammonium carbonate and subsequent reduction of the N(CH2CONMe2)3intermediate by lithium aluminum deuteride has afforded N[CH2CD2N(CH3)2]3or (d6‐arm)‐Me6TREN in three steps and 52 % overall yield. A similar protocol from 2‐bromo‐N,N‐dimethyl‐d2‐acetamide, obtained in two steps fromd4‐acetic acid, with reduction of the N(CD2CONMe2)3intermediate by lithium aluminum hydride has afforded N[CD2CH2N(CH3)2]3or (d6‐cap)‐Me6TREN in four steps and 13 % overall yield from CD3COOD. 
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