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With potassium tert-butylate; In tert-butyl alcohol; for 1.0h;Heating / reflux;
A mixture of (S)- (-)-3- (3-TERT-BUTYLAMINO)-1, 2-propanediol, (2. 0g, 13.59 mole) and 3, 4-DICHLORO-L, 2,5-thiadiazole (2. 11G, 13.59 mole) in anhydrous tert- butanol (10 ML) was heated to reflux under nitrogen. Potassium tert-butoxide solution in tert-butanol (1.0 M, 13.6 mL, 13.6 MMOLE) was then added and the mixture was refluxed for 60 min. The mixture was cooled to room temperature and filtered. The filtrate was concentrated to give brown-red oil (3.49 g, yield 96.6%). Purity by LC was 93.2% at 254 nm. MS (ESI, %): M/Z = 266 (M+1, 100)
a. 30 g of (R)-glyceraldehyde, 36 cc of tert. butylamine in 800 cc of ethanol are hydrogenated over 8 g of 10 % palladium/carbon with H2 for 4 hours, the catalyst is filtered off and the solution is concentrated. (S)-1-tert.butylamino-2,3-dihydroxy-propane is obtained from ethyl acetate/ether (2:1) in the form of crystals having a M.P. of 76-81. [alpha] 20546 = -11.8 (c = 2.0; methanol).
16
[ 30315-46-9 ]
[ 30315-49-2 ]
Yield
Reaction Conditions
Operation in experiment
With benzaldehyde; In water; benzene;
b. 22 g of <strong>[30315-46-9](S)-1-tert.butylamino-2,3-dihydroxypropane</strong>, 20.7 g of benzaldehyde and 46 cc of benzene are heated at reflux in a water separator for 16 hours. The benzene and benzaldehyde are removed by distillation and the residue is distilled in a high vacuum. (S)-3-tert. butyl-5-hydroxy-methyl-2-phenyloxazolidine is obtained as yellowish oil (B.P. 110-125 at 0.01 mm of Hg); [alpha]20546 = 17.8 (c = 1.99; chloroform).
General procedure: To a solution of racemic acid 1 (5.68 mg, 0.04 mmol, 1 equiv) in IPA (0.2 mL, 0.2 M) was added the chiral base (0.04 mmol, 1 equiv as a 0.2 M stock solution in IPA). The resulting mixture was heated at 70 C for 15 min to solubilize all the solids, and then allowed to cool naturally to ambient temperature with stirring overnight. Overall, 23 precipitates were obtained from the 80 combinations. The enantiomeric excess of the solid precipitate and the liquor for each reaction was analyzed by SFC.
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