(S)-dibenzyl 1-(1-hydroxy-3-(tetrahydro-2H-pyran-4-yl)propan-2-yl)hydrazine-1,2-dicarboxylate → 2-Hydrazino-3-(tetrahydro-pyran-4-yl)-propan-1-ol

To a solution of (S)-dibenzyl 1-(1-hydroxy-3-(tetrahydro-2H-pyran-4-yl)propan-2-yl)hydrazine-1,2-dicarboxylate (16.52 g, 0.0374 mol) in methanol (320 mL) was added Pd(OH)2/C (1.65 g). The reaction flask was evacuated and filled with H2. Stirring was continued until the starting material had disappeared. The mixture was filtered through celite, and the filter cake was washed with MeOH (2×30 mL). The combined organic solvent was dried over Na2SO4, and concentrated in vacuum to give 2-hydrazino-3-(tetrahydro-pyran-4-yl)-propan-1-ol (6.15 g, 94%), which was used for the next step without purification. 1H NMR (CD3OD) δ 1.2-1.7 (m, 7H), 2.2-2.7 (s, 4H), 2.8-2.9 (m, 1H), 3.3-3.4 (m, 3H), 3.7-3.8 (m, 1H), 3.9-4.0 (m, 2H).

1. customThe reaction flask was evacuated
2. additionfilled with H2
3. filtrationThe mixture was filtered through celite
4. washthe filter cake was washed with MeOH (2×30 mL)
5. dry with materialThe combined organic solvent was dried over Na2SO4
6. concentrationconcentrated in vacuum

ORD record

ord-90e5d22b51194ab0ac55f18be0e9fc6e

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07872028B2