rac-tert-butyl (3R,4R)-3-({[(benzyloxy)carbonyl]amino}methyl)-4-hydroxypyrrolidine-1-carboxylate → cis-1-Boc-3-hydroxy-4-aminomethylpyrrolidine
Reaktionsgleichung
[OH:1][C@H:2]1[C@@H:6]([CH2:7][NH:8]C(OCC2C=CC=CC=2)=O)[CH2:5][N:4]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:3]1>CO>[NH2:8][CH2:7][C@@H:6]1[C@H:2]([OH:1])[CH2:3][N:4]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:5]1Komponenten
3
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Dissolve 1,1-dimethylethyl(3S,4S)-3-hydroxy-4-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinecarboxylate (0.75 g, 2.14 mmol) in methanol (10 mL). Add 20% PdOH (catalytic) and subject to H at 55 PSI on a Parr hydrogenation apparatus. The solution was filtered through a plug of celite and concentrated under reduced pressure to yield an oil. (0.712 g, quantitative) LCMS: m/z 133.2 (MH+).