Methanol → HCID 178491041, compound

Participants

Reaction Steps

A stirred solution of ethyl 3-(3-cyclopentyloxy-4-methoxybenzylamino-pyrazole-4-carboxylate) (from EXAMPLE 12) (5.4 g, 0.015 mol) in THF (50 mL) at 0° was treated with sodium bis (2-methoxyethoxy)aluminum hydride (0.03 mole), 9 mL of 3.4 M solution in toluene. After 3 hours, another 9 mL portion of the sodium bis(2-methoxy-ethoxy)aluminum hydride solution (0.03 mol) was added. The reaction was stirred overnight at room temperature and methanol (20 mL) was added. The reaction mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate extracts were washed with water and evaporated under reduced pressure. The residue crystallized upon trituration with hexanes. Pure title compound (1.7 g, 38%), mp 76-77°, was obtained after two crystallizations from methyl t-butylether.

Provenance & Evidence