137032-20-3Relevant academic research and scientific papers
p-Hydroxymethadone: Synthesis, Crystal Structure and CD Properties
Brine, George A.,Boldt, Karl G.,Prakash, Doriswamy,Kotchmar, Dennis J.,Bondeson, Virginia C.,et al.
, p. 1809 - 1814 (2007/10/02)
Alkylation of 2-chloro-N,N-dimethylpropylamine 2 with the lithium salt derived from 2-(p-methoxyphenyl)-2-phenylacetonitrile 1 afforded a mixture of p-methoxymethadone nitrile 3 and p-methoxyisomethadone nitrile 4.The nitriles were separated chromatographically and the amino nitrile 3 was converted subsequently into the diastereoisomeric p-hydroxymethadone 8 hydrochlorides.Careful recrystallization afforded a separation of the (4RS,6RS)- and (4RS,6SR)-p-hydroxymethadone hydrochlorides.Repetition of the synthesis using (R)-2-chloro-N,N-dimethylpropylamine, derived in three steps from (S)-dilactide 9, yielded the (4S,6S)- and (4R,6S)-p-hydroxymethadone hydrochlorides, which were also separated by fractional crystallization.The absolute configuration of the products was verified by X-ray crystallography.The (4R,6S) salt exhibited a more intense Cotton effect than (S)-methadone hydrochloride while the (4S,6S) salt showed a less intense Cotton effect and less fine structure in the λ 260-275 nm range.
