Betulinic Acid → Dihydrobetulinic Acid

HRID 2405500Notes

Reaction equation

HRID 2405500 reaction equation
[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]

Participants

5

Reactant 1

HCID 64971Betulinic Acid

Product 1

HCID 65319Dihydrobetulinic Acid

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Sources & evidence

ORD record
ord-4b23711617f14287b7f5212e1cdddaba
Source dataset
uspto-grants-2014_08
Patent number
US08802661B2

Reaction notes

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