Trimethylsilyl cyanide → [5-(2-Amino-1-hydroxy-ethyl)-thiazol-2-yl]-carbamic acid tert-butyl ester

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Reaction Steps

To a solution of compound 62.3 (4.5 mmol) in dichloromethane is added trimethylsilyl cyanide (“TMSCN”; 2.1 equivalents) and ZnI2 (10% mol). After stirring at room temperature overnight, the reaction is concentrated under vacuum. The crude cyanohydrin is dissolved in THF and treated with AlH3 (2.2 equivalents of a 0.5 M solution in THF). After stirring for 15 minutes, the reaction is quenched with the addition of saturated aqueous Na2SO4, is filtered through a pad of Celite, is dried and concentrated. Purification by flash column chromatography on silica gel (10% 7.0 M NH3/MeOH in dichloromethane) provides [5-(2-amino-1-hydroxy-ethyl)-thiazol-2-yl]-carbamic acid tert-butyl ester (compound 62.4).

Provenance & Evidence