Reaktion #2288920

Reaktionsgleichung

compound 27

(3S,4aR,6aR,7aS,10aR,11aR,11bR)-7a,11b-Dimethyl-3-hydroxy-2,3,4,4a,5,6,6a,7,7a,10,10a,11,11a,11b-tetradeca hydro-1H-cyclopenta[b]phenanthren-8-carbonitrile

→

compound 28

Ausbeute 90.0%

(3S,4aR,6aR,7aS,8S,10aS,11aR,11bR)-Hexadecahydro-7a,11b-dimethyl-3-hydroxy-1H-cyclopenta[b]phenanthrene-8-carbonitrile

Ausbeute 90.0%

Lösungsmittel

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction was filtered through Celite which
2. 2
   Waschenwas washed with EtOAc (100 mL)
3. 3
   SonstigeSolvents were removed
4. 4
   Sonstigethe residue was purified by flash column chromatography (silica gel eluted with 10% EtOAc in hexanes)

Vorschrift

To a solution of the compound 27 (60 mg, 0.2 mmol) in EtOAc (40 mL) was added Pd/C (30 mg). Hydrogenation was carried out under 5 atm H2 at room temperature for 3 h. The reaction was filtered through Celite which was washed with EtOAc (100 mL). Solvents were removed and the residue was purified by flash column chromatography (silica gel eluted with 10% EtOAc in hexanes) to afford compound 28 (54 mg, 90%): mp 145-147° C., [α]D25 +45.3 (c 0.23, CHCl3); 1H NMR (CDCl3) δ 4.05 (s, br, 1H), 2.27 (t, J=9.3 Hz, 1H), 0.89 (s, 3H), 0.78 (s, 3H); 13C NMR (CDCl3) δ 121.5, 66.5, 54.4, 48.6, 45.6, 44.3, 39.9, 39.2, 36.4, 35.7, 34.8, 32.1, 32.0, 28.8, 28.7, 26.6, 26.5, 24.1, 14.4, 11.2; IR νmax 3434, 2235, 1449 cm−1. Anal. Calcd for (C20H31NO): C, 79.68; H, 10.36; N, 4.65. Found: C, 79.47; H, 10.67; N, 4.77.

Quelle