Ammonium → 4-(((Tert-butyldiphenylsilyl)oxy)methyl)aniline

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To a stirred solution of 2a (5.00 g, 12.80 mmol) in ethanol (100 mL) was added Pd/C 10%(1.50 g) and ammonium fornate (4.60 g) in one portion at 20° C. After 1.5 h the catalyst was removed by filtration, the filtrate concentrated under vacuum and the residue partitioned between EtOAc:H2O. The organic layer was dried (MgSO4) and concentrated to give 3a as an oil yield: 4.24 g (91%) νmax /cm-1 (film): 3433, 3378 (NH2), 2931, 2857 (CH2, asym. sym.): 1H-NMR, δH : 1.00 (s, 9H. t-Bu), 4.57 (s, 2H. CH2), 4.98 (s broad, 2H, NH2), 6.52 (d, 2H, J=8.25 Hz, Harom3+5), 6.96 (d, 2H, Harom2+6), 7.42-7.46 (m, 5H, Ph), 7.62-7.65 (m, 5H, Ph): MS, (EI), (361.56); m/z: 361 (M+, 8), 304 (M-t-Bu, 100), 199 (Ph2SiOH+, 100); anal (C23H27NOSi), C, H, N.

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