Methanol → HCID 57934815, compound

Participants

Reaction Steps

A solution of lithium aluminium hydride (1M in ether, 0.3 ml, 0.3 mmol) was added dropwise to a stirred solution of 4-[3-(2,4-Bis-benzyloxy-5-chloro-phenyl)-5-isobutoxycarbonyl-1-(toluene-4-sulfonyl)-1H-pyrazol-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (90 mg, 0.11 mmol) [prepared by use of the lithiation chemistry in the preceding example] in anhydrous diethyl ether (2 ml) at room temperature, under a nitrogen atmosphere. The suspension was stirred 2 h then sodium hydroxide solution (1M, 3 drops) was added, followed by methanol (0.5 ml). The mixture was partitioned between water (30 ml) and ethyl acetate (2×20 ml), and the combined organic phases were dried over magnesium sulphate, then concentrated in vacuo to give 4-[3-(2,4-Bis-benzyloxy-5-chloro-phenyl)-5-hydroxymethyl-1-(toluene-4-sulfonyl)-1H-pyrazol-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (58 mg, 88%)

Provenance & Evidence