Prototypical Reagent for the Synthesis of Substituted Hydrazines

✍ Scribed by Dr. Uno Mäeorg; Dr. Leif Grehn; Dr. Ulf Ragnarsson

• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 484 KB
• Volume: 35
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.199626261

✦ Synopsis

gelatin * solids yield. 'H NMR (270 MHz. CDCI,): b =1.42 (s, 18H. NBoc,), 1.49 (s, 9H. NHBoc), 5.26 (5, 2H, CH,Ph), 7. 30-7.41 (brm, 5 H, Ph). Compound 3, dissolved in CH,OH (500 mL). was hydrogenolyzed over PdjC (S%/carbon. 1.2 g) for 3 h. When TLC indicated complete reaction, the catalyst was filtered off (Celite). The solvent was removed to give a solid, which was recrystallized from light petroleum ether to afford pure 4 as white crystals; yield: 16.3 g (82% from 1); m.p. 104.5-105.5"C; pure by TLC. 'H NMR (270 MHz, CDCI,, 2 0 °C TMS): 6 = 1.48/1.51 (2 signals. together 27H. Boc). 6.47/6.18 (2 br. signals. together 1 H. NH); correct C,H,N analysis.