Sodium borodeuteride labeling

The most commonly used method for synthesizing organotin hydrides with a hydrogen isotope bonded to the tin atom is to reduce the appropriate chlorostannanes with labelled hydride reagents, such as lithium aluminium deuteride or sodium borodeuteride. For example, tributylchlorostannane can be reduced with lithium aluminium deuteride42-45 or deuterated or tritiated sodium borohydride46 to give tributyltin deuteride and tritiated tributyltin hydride, respectively (equations 40 and 41). 

Application of alumina-supported sodium borodeuteride under the reaction conditions described by Varma26 provided deuterated alcohols from aldehydes and ketones with a high degree of deuterium incorporation. The method is thus suitable for isotopic labelling procedures (Scheme 4.12)32. 

Figure 3 The total ion ourrent ohromatogram obtained for the organic acids isolated from the sodium borodeuteride-treated urine of a patient with maple syrup urine disease. The ratios of the H-labelled to unlabelled analogues for 2-hydroxyisovaleric acid, 2-hydroxyisooaproio acid and the two 2-hydroxy-3-methylvaleric acid diastereomers are respectively 0.24, 34.5, 30.0 and 3.70.

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