WO 2011019801

http://www.google.im/patents/WO2011019801A1?cl=en
Intermediate 2
1,1-dimethylethyl [(15)-l-formyl-3-phenylpropyl] carbamate

To a solution of 1,1-dimethylethyl ((15)-l-{[methyl(methyloxy)amino]carbonyl}-3- phenylpropyl)carbamate (86.0 g, 0.266 mol) in THF (600 mL) at 0 ⁰C was added LiAlH₄ (13.17 g, 0.347 mol). The reaction mixture was stirred at 0 ⁰C for 1 h, quenched with Na₂SO₄-IO H₂O (40.0 g in 600 mL of water), and stirred for an additional 2 h. The reaction mixture was diluted with Et₂O (200 mL) and the layers were separated. The aqueous layer was extracted with Et₂O (3 x 200 mL). The combined organic layers were washed with 1 M aq. HCl (2 x 100 mL), saturated aq. NaHCO₃ (2 x 100 mL), and brine, dried over Na₂SO₄, filtered, and concentrated in vacuo to afford the title compound (60 g, 86%), which was carried to the next step without further purification. ¹H NMR (400 MHz, DMSO-J₆) δ ppm 9.55 (s, IH), 7.30 - 7.18 (m, 5H), 5.08 (d, 2H), 4.25 (m, IH), 2.71 (m, IH), 2.24 (m, IH), 1.84 (m, IH), 1.46 (s, 9H).