Aluminium lithium hydride → {(S)-3-[3-(4-chlorophenoxy)-azetidin-1-yl]-1-hydroxymethyl-propyl}-carbamic acid tert-butyl ester

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Reaction Steps

A solution of (S)-2-tert-butoxycarbonylamino-4-[3-(4-chloro-phenoxy)-azetidin-1-yl]4-oxo-butyric acid benzyl ester (1.0 g, 2.04 mmol) in dry THF (10 ml) is treated with a 1M solution of lithium aluminium hydride (5.1 ml) keeping the temperature between 20-30° C. using an ice-water bath. The reaction mixture is stirred at ambient temperature under argon for 2 hours, then quenched by addition of saturated aqueous Na2SO4 and filtered through a celite™ filter. The filtrate is partitioned between ethylacetate and saturated brine. The ethylacetate phase dried over MgSO4 and evaporated. The crude product is purified by flash silica chromatography (elution with 5:95 methanol/dichloromethane) to afford {(S)-3-[3-(4-chloro-phenoxy)-azetidin-1-yl]-1-hydroxymethyl-propyl}-carbamic acid tert-butyl ester. [MH]+ 371.0.

Provenance & Evidence