Many thanks Dan. Is that a chiral catalyst I see on the first page? I was attempting to figure out a way where the actual hydride is chiral so that no catalyst is required. What do you think of:
Paper Asymmetric syntheses. Part 2. Reduction of ketones with chiral sodium borohydride-lactic acid derivative systems
Giorgio Bianchi, Fiorella Achilli, Anna Gamba and Dina Vercesi
J. Chem. Soc., Perkin Trans. 1, 1988, 417-422
They only claim a 38.3%ee but, if applied to the synthesis of sertraline, it could potentially reduce costs. Also, while sodium triacetoxyborohydride has very poor solubility in almost all solvents so I wonder if those 3 extra -OH groups would make it soluble in the ethanol used in that cool Green Chemistry route. OK, the imine is insoluble in ethanol, but will a dissolved reducing agent still work on the surface?
I REALLY appreciate your input. I slept 4 hours and used Reaxys, which misses SO much stuff and I will rind my buddy at a different uni where they have SciFinder to see what he can dig up.
Wouldn't it be great if we could knock off another 20% off the production costs for sertraline - just on this board ;-)