Borane;tetrahydrofuran → N-[3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-(hydroxymethyl)phenyl]-N-propylmethanesulfonamide

Beteiligte Stoffe

Reaktionsschritte

To a solution of 3({2-[(tert-butoxycarbonyl)amino]-2-methyl-3-phenylpropoxy}methyl)-5-[(methylsulfonyl)(propyl)amino]benzoic acid (intermediate XI, 145 mg, 0.271 mmol) in THF (2 mL) cooled to 0° C. was added BH3-THF (1.356 mL, 1.356 mmol, 1 M in THP). After 10 min, the reaction mixture was allowed to warm to rt and stirred for 60 h. The reaction mixture was cooled back down to 0° C. and carefully quenched with MeOH. The mixture was concentrated to half its original volume and diluted with EtOAc and water. Following dilution, the organic layer was extracted, washed with sat. aq. NaHCO3 and brine, dried over sodium sulfate and concentrated in vacuo to provide N-[3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-(hydroxymethyl)phenyl]-N-propylmethanesulfonamide as a white foam. 1H NMR (400 MHz, CDCl3) δ 7.33 (s, 1H), 7.29 (s, 1H), 7.28-7.20 (m, 4H), 7.17-7.13 (m, 2H), 4.74 (s, 2H), 4.60-4.51 (m, 3H), 3.63 (t, J=7.2 Hz, 2H), 3.53 (A of AB, d, J=8.8 Hz, 1H), 3.43 (B of AB, d, J=8.8 Hz, 1H), 3.12 (A of AB, d, J=13.2 Hz, 1H), 2.93 (B of AB, d, J=13.2 Hz, 1H), 2.88 (s, 3H), 1.55-1.45 (m, 2H), 1.46 (s, 9H), 1.25 (s, 3H), 0.91 (t, J=7.3 Hz, 3H).

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