Ethyl, amine oxalic acid

Aminopropane, diazomethane, dimethylamine, 1,1-dimethylhydrazine, ethyl-amine, ethyldimethylamine, ethylene imine, ethylmercury chloride, formaldehyde, carbon disulfide, methanethiol, methylamine, methyl isocyanate, oxalic acid dinitrile, phosgene. 

Wock-Hardt Ltd.54 reported a manufacturing process for the preparation of 2 (Scheme 8). In their approach, reductive amination of ketone 41 with dimethylamine hydrochloride using NaCNBH3 afforded amine 42 in 69% yield. The phenol was acylated with iV-ethyl-/V-methyl carbamoyl chloride (40) using KO/-Bu as the base instead of NaH to provide racemic carbamate 2 in 88% yield (98% pure by HPLC). Racemic 2 was further purified by making the oxalate salt, which provided 2 as a colorless crystalline oxalate salt in 100% purity. Resolution with DTTA followed by salt formation with tartaric acid afforded chiral tartrate salt 2. The overall yield of this process was 20%. 

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