Nitrogen → {1-[2-(1-Hydroxy-ethyl)-oxazol-4-ylmethyl]-1H-pyrazol-4-yl}-carbamic acid 2-chloro-benzyl ester

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Reaction Conditions

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [1-(2-dihydroxymethyl-oxazol-4-ylmethyl)-1H-pyrazol-4-yl]-carbamic acid 2-chloro-benzyl ester (212 mg, 0.56 mmol) in CH2Cl2 (4.0 mL) was treated at 0° C. with trimethylaluminum (1.40 mL of a 2M solution in toluene, 2.80 mmol). The reaction mixture was then stirred at 0° C. for 1 h and at rt for 16 h. Sat. aq. NH4Cl was then added and the aq. layer was extracted with CH2Cl2 (3×10 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a pale yellow oil. TLC: rf (1:1 hept-EA)=0.28. LC-MS-conditions 02: tR=0.86 min, [M+H]+=377.17.

Provenance & Evidence