Reaktion #160797

Reaktionsgleichung

(4aR,8aS)-4-(phenylamino)octahydroquinolin-4a(2H)-ol

NaHCO3

3-methylbutanoyl chloride

→

title compound

1-[(4aS,8aS)-4a-hydroxy-4-(phenylamino)octahydroquinolin-1(2H)-yl]-3-methylbutan-1-one

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe mixture was diluted with sat'd
2. 2
   Extraktionaq. NaHCO3 and CH2Cl2 and extracted 3× with CH2Cl2
3. 3
   TrocknenThe combined organics were dried (anted. Na2SO4)
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue was purified by column chromatography

Vorschrift

To a mixture of (4aR,8aS)-4-(phenylamino)octahydroquinolin-4a(2H)-ol (20 mg, 0.081 mmol) in 1:1 CH2Cl2:sat'd. aq. NaHCO3 (3 mL) was added 3-methylbutanoyl chloride (0.049 g, 0.406 mmol). The mixture was stirred at rt for 1 hr. The mixture was diluted with sat'd. aq. NaHCO3 and CH2Cl2 and extracted 3× with CH2Cl2. The combined organics were dried (anted. Na2SO4), filtered, and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (400 MHz, CDCl3) δ 7.22-7.40 (m, 5H), 4.38 (d, 1H, J=10.4 Hz), 3.96 (d, 1H, J=10.2 Hz), 3.35 (t, 1H, J=9.4 Hz), 2.62-2.85 (m, 2H), 1.15-2.40 (m, 12H), 0.81-0.99 (m, 6H). HRMS (ES) m/z M+H calc'd:331.2380. found: 331.2379.

Quelle