反应详情

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.

1. custombetween 20-30° C.
2. customquenched by addition of saturated aqueous Na2SO4
3. filtrationfiltered through a celite™
4. filtrationfilter
5. customThe filtrate is partitioned between ethylacetate and saturated brine
6. dry with materialThe ethylacetate phase dried over MgSO4
7. customevaporated
8. customThe crude product is purified by flash silica chromatography (elution with 5:95 methanol/dichloromethane)