2921-13-3Relevant academic research and scientific papers
METHOD OF PREPARING AN ALKYLAMINE DERIVATIVE
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Page/Page column 6, (2012/03/10)
The present invention provides a method of preparing an alkylamine derivates which hardly generates impurities and enables mass production with high purity.
Asymmetric synthesis of (S)-(+)-carnitine and analogs
Jain, Rajendra P,Williams, Robert M
, p. 6505 - 6509 (2007/10/03)
A general asymmetric route to enantiomerically pure (S)-(+)-carnitine and analogs has been investigated that involves mono-addition of organometallic reagents to the lactone carbonyl group of (5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin- 2-one and Lewis acid promoted stereoselective allylation of the resulting hemiacetals. The diastereomerically pure allyl oxazines thus obtained were readily converted into enantiomerically pure (S)-(+)-carnitine and two substituted analogs.
Asymmetric synthesis of (R)-(-)-carnitine
Jain, Rajendra P.,Williams, Robert M.
, p. 4437 - 4440 (2007/10/03)
A TiCl4-promoted Mukaiyama-type aldol reaction of the ketenesilyl acetal of ethyl acetate with the lactone carbonyl of (5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin- 2-one (1) proceeds with a high degree of diastereoselectivity. The TBDMS-protected hemiketal thus obtained was efficiently converted into highly enantiomerically enriched (R)-(-)-carnitine by following an elimination-reduction protocol. This approach further demonstrates the utility of commercially available glycine template 1 as a potential substrate for the asymmetric synthesis of both enantiomers of carnitine.
