Development of a Scalable Process for α‑Amino-ω-methoxyl-dodecaethylene Glycol

We have developed a process for the efficient and scalable preparation of hetero­function­alized dodeca­ethylene glycol from the readily available tetra­ethylene glycol and its macro­cyclic sulfate. By employing the benzyl group as both a protecting group and a separative tag, multiple chromato­graphic separations were avoided. With this method, α-amino-ω-methyl-dodeca­ethylene glycol was prepared on a 53 g scale with high purity and 61% overall yield in eight steps and one chromato­graphic separation