Ethyl Acetate → (R)-Methyl 4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-acetoxy-10,13-dimethyl-12-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate

HRID 385170Notes

Reaction equation

HRID 385170 reaction equation
[OH:1][C@@H:2]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C:23]2=[CH:22][C:21](=[O:28])[C@@:20]2([CH3:29])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:19])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:3]1.[CH3:30][CH2:31][O:32]C(C)=O>[Pd]>[C:31]([O:1][C@@H:2]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:23]2[CH2:22][C:21](=[O:28])[C@@:20]2([CH3:29])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:19])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:3]1)(=[O:32])[CH3:30]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 255793Deoxycholic Acid Impurity 39

Product 1

HCID 21632880(R)-Methyl 4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-acetoxy-10,13-dimethyl-12-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoateYield 80%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

10% Pd/C (900 mg) was added to a solution of compound 1.9a (2.0 g, 4.5 mmol) in EtOAc (150 mL) and the resulting slurry was hydrogenated in a Parr apparatus (50 psi) at 50° C. for 16 h. At this point the reaction was determined to be complete by TLC. The mixture was filtered through a small plug of Celite® and the solvent was removed under vacuum, providing compound 2.0a (1.6 g, 80% yield) as a white solid.

Workup

  1. filtrationThe mixture was filtered through a small plug of Celite®
  2. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-d4fff63463204acf814223550f973fed
Source dataset
uspto-grants-2013_02
Patent number
US08367852B2

Reaction notes

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