Betulinic Acid → Dihydrobetulinic Acid
反応式
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@:7]3([CH3:31])[C@@H:16]2[CH2:15][CH2:14][C@H:13]2[C@@:8]3([CH3:30])[CH2:9][CH2:10][C@@:11]3([C:27]([OH:29])=[O:28])[CH2:23][CH2:22][C@@H:21]([C:24]([CH3:26])=[CH2:25])[C@@H:12]32)[C:3]1([CH3:33])[CH3:32]>C(OCC)(=O)C.CO.[Pd]>[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@:7]3([CH3:31])[C@@H:16]2[CH2:15][CH2:14][C@H:13]2[C@@:8]3([CH3:30])[CH2:9][CH2:10][C@@:11]3([C:27]([OH:29])=[O:28])[CH2:23][CH2:22][C@@H:21]([CH:24]([CH3:26])[CH3:25])[C@@H:12]32)[C:3]1([CH3:32])[CH3:33]参加物
5
実験手順
A mixture of (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid (4 g, 8.76 mmol) and 10% Pd/C (1.398 g, 1.314 mmol) in ethyl acetate (80 mL) and MeOH (30 mL) was connected to Parr Shaker and shaked for 18 h under 45 psi at room temperature. LCMS indicated the formation of desired product. The reaction mixture was filtered through celite and the filtrates were concentrated under reduced pressure to give the title compound as white solid (3 g, 75%). LCMS: m/e 457.27 (M−H)−, 2.40 min (method 1).