tert-Butyl 2-{1-[4-(ethoxycarbonyl)phenyl]ethyl}hydrazine-1-carboxylate → HCID 86602021, compound

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Reaction Steps

tert-Butyl 2-{1-[4-(ethoxycarbonyl)phenyl]ethyl}hydrazinecarboxylate (29 g, 94 mmol) was treated with 100 ml of TFA-DCM-triisopropylsilane (20:20:1) at room temperature for one hour. The mixture was concentrated under reduced pressure, and the residue was dissolved in water (100 ml), washed with DCM 2×. The DCM was back extracted with water 3×. HCl (5N, 20 ml) was added to the combined water solution and concentrated to 50 ml. CH3CN (50 ml) was added and this was lyophilized to give 22.7 g of {1-[4-(ethoxycarbonyl)phenyl]ethyl}-hydrazinium chloride. NMR (500 MHz, acetone-d6) δ: 1.34 (t, J=7.1 Hz, 3H); 1.67 (d, J=6.8 Hz, 3H); 4.33 (q, J=7.1 Hz, 2H), 4.97 (q, J=6.8 Hz, 1H), 7.76 (d, J=8.5 Hz, 2H), 7.97 (d, J=8.5 Hz, 2H). MS C11H16N2O2 Cald: 208.12; Obsd (M+1): 209.19.

Provenance & Evidence