Abstract:
:Numbers of resolving factors were investigated to improve resolution of venlafaxine 1. An effective resolving agent, O,O'-di-p-toluoyl-(R, R)-tartaric acid 2, was screened using similar method of 'Dutch resolution' from tartaric acid derivatives. The resolution efficiency was up to 88.4%, when the ratio of rac-1 and 2 was 1:0.8 in THF with little water (10:1 v/v). Enantiomerically pure venlafaxine was prepared with 99.1% ee in 82.2% yield. The chiral resolution mechanism was first explained through X-ray crystallographic study. One diastereomeric salt with well solubility forms a columnar supramolecular structure as the acidic salt (R)-1·2, while the other diastereomeric salt with less solubility forms a multilayered sandwich supramolecular structure by enantio-differentiation self-assembly as the neutral salt 2(S)-1·2. The water molecules play a key role in the optical resolution, as indicated by the special structures of the diastereomeric salts.
journal_name
Chiralityjournal_title
Chiralityauthors
Liu ZJ,Liu H,Chen XW,Lin M,Hu Y,Tuo X,Yuan ZY,Sun XXdoi
10.1002/chir.22790subject
Has Abstractpub_date
2018-03-01 00:00:00pages
268-274issue
3eissn
0899-0042issn
1520-636Xjournal_volume
30pub_type
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