1: 58 percent / LiAlH4 / tetrahydrofuran / 0.5 h / -78 °C 2: 1.) H2, 2.) Et3N, TBTU / 1.) Pd/C / 1.) MeOH, 2.) MeCN View Scheme

1: 32 percent / LiAlH4 / tetrahydrofuran / 0.5 h / -78 °C 2: 93 percent / H2 / Pd/C / tetrahydrofuran / 48 h / 3800 Torr View Scheme

1: 32 percent / LiAlH4 / tetrahydrofuran / 0.5 h / -78 °C 2: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 1 h, 3.) 4 deg C, overnight 3: 91 percent / AIBN, Bu3SnH / xylene / 1 h / Heating 4: 95 percent / H2 / Pd(OH)2/C / tetrahydrofuran / 25 h / 3800 Torr View Scheme