And Troger’s base

The hydrogenation of ehtyl pyurvate (EtPy) was carried out at 23 °C in a SS autoclave equipped with an injection chamber for separate introduction of the modifier Cinchonidine (CD) and Troger s base (TB) was used as modifiers. Different batches of EtPy, (Fluka) and Pt/Al203 catalysts (Engelhard E 4759, 5 %w Pt, Dpt = 25 %) were used. Experimental details incliding GC analysis can be found elsewhere [3,12]. The optical yield was calculated as e.e. = ([R]-[S])/([R]+[S]). The e.e. values were corrected for the amount of racemic product formed in minor amount in the reactor prior to the injection of CD. 

Benzoin, methylbenzoin, ethylbenzoin, isopropylbenzoin, benzoin oxime, cyclobutyldianilide carbamate, 1,1 -binaphthyl-2,2 -diol, trans-stilbene oxide, and Trogers s base Polymethacrylate 104, 96... 

Figure 14.7 Staircase frontal analysis of (+)-and (-)- Troger s base, (a) (+) enantiomer,...

SMB and column chromatography for plasmid DNA purification and Troger s base enantiomer separation Maximization of productivity and minimization of solvent consumption. NSGA Optimization results show that SMB is better tiian column chromatography for the two applications studied. Paredes and Mazzotti (2007)... 

Fig. 9 Separation of tran -l-amino-2-indanol (Z ) and Troger s base right) on CF6 CSPs (columns 25 cm, 4.6 mm i.d.) derivatized in three different ways (a) and (d), low-degree methyl carbamate derivatization (b) and (e), low-degree 3,5-dimethylphenyl carbamate deriva-tization (c) and (f), high-degree 3,5-dimethylphenyl carbamate derivatization. Mobile phases left, acetonitrile/methanol/acetic acid/triethylamine 60/40/0.3/0.2 (70/30/0.3/0.2% v/v for (c)) right, heptane/ethanol 10130% v/v and 1 mL/min. UV detection 254 nm...

FIGURE 4.2 Chemical structures of racemic alcohols (and Troger s base) tested on CTB/silica gel plates. 

Complexes (65) and (66) result from the reaction of IrCl3 with inah and PPh3 (inah = isonicotinic acid hydrazide).92 Reaction of Troger s base (tb) (67) with IrCl3 yields dark violet tb 2IrCl3 (6S).93 (68) was not catalytically active towards the hydrosilylation of alkynes. 

Figure 3.12 Enantioseparation of TrOger s base on (a) microcrystalline cellulose triacetate (CTA I) and (b) 21 coated on silica gel. Column, 25 x 0.46 (i.d.) cm eluent ethanol-HoO (7/3) flow rate, 0.5 ml/min).

Figure 16.17 Amine-terminated polypropylene imine) dendrimers act as tridentate ligands for the complexation of transition metals [217] (a), and can function as templates for the assembly of Troger s base dizinc(ll) bis-porphyrin molecules, (b) [218]...

Acids and bases. These can be converted to various salts. For example, the absolute configuration of dimethyl (M)-5,6,8,10-tetramethyl-l,2-heptalenedicarboxylate (p 404) was determined by X-ray analysis of its (+)-ephedrine salt84, and the absolute configuration of Troger s base (p 404) by X-ray analysis of a salt with an acid of known configuration87. 

This material has been successfully applied for the enantioseparation of Troger s base and tetrahydropalmatine, and for the separation of anaesthetic drugs, where the... 

CSPs (CTA-I and CTA-II) have inverse selectivity for Troger s base and trans-1,2-diphenyloxirane racemates. These characteristics of CTA CSPs are responsible for good chiral resolution of small cychc carbonyl compounds [42]. In 2001 Aboul-Enein and Ah [63] observed the reversed order of elution of nebivolol on a Chiralpak AD column when ethanol and 2-propanol were used separately as the mobile phases. Table 1 presents selectivity data for the polysaccharide-based CSPs. Okamoto et al. [42] observed that the introduction of a methyl group at the para position of cellulose tribenzoate results in a dramatic shift of the structural selectivity toward aromatic compounds with larger skeletons, and its selectivity was rather similar to that of cellulose tricinnamate. 

FIGURE 16 The chemical structures of some drugs resolved on different CSPs based on a- and /1-cyclodextrin derivatives (Fig. 15) Troger s base (I), tra .s-2,.1-diphenyloxirane (II), l-(9-anthryl)-2,2,2-trifluoroethanol (III), 1,2,2,2-tetraphenylethanol (IV), 2,2 -dihy-droxy-6,6-dimethylbiphenyl (V), 2-phenylcyclohexanone (VI), flavanone (VII), benzoin (VIII), and tnms -cyclopropanedicarboxylic acid anilide (IX). (From Ref. 49.)... 

B. Chiral Resolution and Optical Properties of Troger s Bases. 23... 

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