(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
Reaktionsgleichung
[OH:1][CH2:2][C@@H:3]([N:11](C(OCC1C=CC=CC=1)=O)[NH:12]C(OCC1C=CC=CC=1)=O)[CH2:4][CH:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1>CO.[OH-].[OH-].[Pd+2]>[NH:11]([CH:3]([CH2:4][CH:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1)[CH2:2][OH:1])[NH2:12]Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
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).