N#N.C([O:5][C:6]([C:8]1[CH:12]=[C:11]([CH2:13][N:14]2[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[N:15]2)[O:10][N:9]=1)=O)C.CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1.C1(C)C=CC=CC=1>[N+:19]([C:17]1[CH:16]=[N:15][N:14]([CH2:13][C:11]2[O:10][N:9]=[C:8]([CH2:6][OH:5])[CH:12]=2)[CH:18]=1)([O-:21])=[O:20]In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-(4-nitro-pyrazol-1-ylmethyl)-isoxazole-3-carboxylic acid ethyl ester (3.477 g, 13.061 mmol) in THF (130.0 mL) was treated dropwise, at −78° C. with DiBAL (44.4 mL of a 1M solution in toluene, 44.41 mmol). The reaction mixture was stirred at −78° C. for 1 h followed by 1 h at rt. Sat. aq. Rochelle's salt (300 mL) was added and the reaction mixture was stirred for 2 h at rt. The aq. layer was extracted with EA (2×300 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (20:80 hept-EA) gave the title compound as a yellow oil. TLC: rf (20:80 hept-EA)=0.33. LC-MS-conditions 02: tR=0.68 min.
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