lithium aluminium tetrahydride in tetrahydrofuran 16 h; Heating;

1: 60 percent / hydroxylamine hydrochloride, pyridine / ethanol / 2 h / Heating 2: 24 mg / LiAlH4 / tetrahydrofuran / 16 h / Heating View Scheme

1: 43 percent / NaBH4 / ethanol / 1.) 50 deg C, 30 min, 2.) RT, 3.5 h 3: 60 percent / hydroxylamine hydrochloride, pyridine / ethanol / 2 h / Heating 4: 24 mg / LiAlH4 / tetrahydrofuran / 16 h / Heating View Scheme

1: 64 percent / sodium periodate, ruthenium trichloride trihydrate / acetonitrile; CCl4; H2O / 1.) reflux, 3 h, 2.) RT, overnight 2: 43 percent / NaBH4 / ethanol / 1.) 50 deg C, 30 min, 2.) RT, 3.5 h 4: 60 percent / hydroxylamine hydrochloride, pyridine / ethanol / 2 h / Heating 5: 24 mg / LiAlH4 / tetrahydrofuran / 16 h / Heating View Scheme

2: 60 percent / hydroxylamine hydrochloride, pyridine / ethanol / 2 h / Heating 3: 24 mg / LiAlH4 / tetrahydrofuran / 16 h / Heating View Scheme