tert-butyl (1R,5S)-3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate → tert-Butyl 3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate
Reaktionsgleichung
[CH3:1][C:2]([O:5][C:6]([N:8]1[C@@H:12]2[CH2:13][C:14]([CH2:16][C@H:9]1[CH2:10][CH2:11]2)=O)=[O:7])([CH3:4])[CH3:3].[BH3-]C#[N:19].[Na+]>CO>[NH2:19][CH:14]1[CH2:16][CH:9]2[N:8]([C:6]([O:5][C:2]([CH3:4])([CH3:3])[CH3:1])=[O:7])[CH:12]([CH2:11][CH2:10]2)[CH2:13]1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A stirred mixture of Boc-nortropinone (287 mg, 1.3 mmol), NH4OAc (1.96 g, 25.5 mmol), NaCNBH3 (800 mg, 12.7 mmol) and MeOH (20 mL) was heated at reflux for 2 h. The mixture was concentrated, the residue was diluted with 0.5 M aq NaOH (30 mL) and extracted with CH2Cl2 (2×50 mL). The combined organic phase was washed with brine (20 mL), dried over Na2SO4 and concentrated to afford tert-butyl 3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate (291 mg, quant) as a mixture of isomers. LC-MS Method 1 tR=0.88 min, m/z=227.