2-Hydrazino-3-(tetrahydro-pyran-4-yl)-propan-1-ol → 2-Amino-3-(oxan-4-yl)propan-1-ol

To a solution of 2-hydrazino-3-(tetrahydro-pyran-4-yl)-propan-1-ol (6.15 g, 0.035 mol) in MeOH (120 mL) was added Raney Ni. The flask was evacuated and equipped with a hydrogen inflated balloon. The flask was dipped into an ultrasound bath filled with water and sonicated for 4 h at rt until the starting material was completely consumed. The mixture was filtered through celite, and the filter cake was washed with MeOH (2×30 mL). Concentration of the filtrate under reduced pressure gave 2-amino-3-(tetrahydro-pyran-4-yl)-propan-1-ol (5.1 g, 91%). 1H NMR (CD3OD) δ 1.2-1.5 (m, 4H), 1.5-1.7 (m, 3H), 1.9-2.2 (s, 3H), 2.9-3.0 (m, 1H), 3.2-3.3 (m, 1H), 3.3-3.4 (m, 2H), 3.5-3.6 (m, 1H), 3.9-4.0 (m, 2H).

1. customThe flask was evacuated
2. customequipped with a hydrogen inflated balloon
3. customThe flask was dipped into an ultrasound bath
4. additionfilled with water
5. customsonicated for 4 h at rt until the starting material
6. customwas completely consumed
7. filtrationThe mixture was filtered through celite
8. washthe filter cake was washed with MeOH (2×30 mL)

ORD record

ord-737da7bf122a4784a76bde6801e1b3c6

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07872028B2