1-Hydroxybenzotriazole → HCID 10637968, compound

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Reaction Steps

To a stirred solution of 1-tert-butyloxycarbonyl-4,4-dimethylpipecolic acid (24.6 g), N,O-dimethylhydroxylamino hydrochloride (12.12 g) and 1-hydroxybenzotriazole (18.09 g) in anhydrous dimethylformamide (400 ml) was added anhydrous triethylamine (30.7 ml) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (21.08 g) and the resulting mixture was stirred at room temperature for 23 hours under a nitrogen atmosphere. Diethyl ether (1 l) was added and the mixture was washed with 1N hydrochloric acid (2×250 ml), 1N sodium hydroxide (1×250 ml), brine (1×200 ml), dried (MgSO4) and concentrated. Flash chromatography (silica gel, hexane-diethyl ether, 40:60) of the residue afforded the title compound (24.1 g) as a white solid; δH (250 MHz, CDCl3) 4.76 (1H, br s), 3.92-3.74 (1H, m), 3.75 (3H, s), 3.58-3.42 (1H, m), 3.19 (3H, s), 1.84 (1H, dd, J=14.0 and 3.3 Hz), 1.64 (1H, dd, J=14.0 and 7.6 Hz), 1.52-1.34 (11H, m and s), 0.94 (3H, s), 0.92 (3H, s); m/z (CI)301 (M+ +1).

Provenance & Evidence