3-Cyclopentyloxy-4-methoxybenzaldehyde → HCID 178491044, compound
Reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH:10]=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:17][C:18]1[C:22]([C:23]([OH:25])=[O:24])=[CH:21][NH:20][N:19]=1.C([BH3-])#N.[Na+]>>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH2:10][NH:17][C:18]2[C:22]([C:23]([OH:25])=[O:24])=[CH:21][NH:20][N:19]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1Participants
4
Procedure
The condensation of 3-cyclopentyloxy-4-methoxybenzaldehyde with 3-amino-4-pyrazolecarboxylic acid in the presence of sodium cyanoborohydride produces 3-(3-cyclopentyloxy-4-methoxybenzyl-amino)-4-pyrazolecarboxylic acid in 48% yield. Treatment with excess borane-tetrahydrofuran complex in tetrahydrofuran solution gives 3-(3-cyclopentyloxy-4-methoxybenzylamino)-4-hydroxymethylpyrazole (Example 1) in 40% yield.