5beta-Chol-9(11)-en-24-oic acid, 3alpha-hydroxy-12-oxo-, methyl ester, 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 1671723Notes

Reaction equation

HRID 1671723 reaction equation
[C:1]([O:4][C@@H:5]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C:26]2=[CH:25][C:24](=[O:31])[C@@:23]2([CH3:32])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:22])[CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:6]1)(=[O:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([O:4][C@@H:5]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:26]2[CH2:25][C:24](=[O:31])[C@@:23]2([CH3:32])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:22])[CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 2400245beta-Chol-9(11)-en-24-oic acid, 3alpha-hydroxy-12-oxo-, methyl ester, acetate

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 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

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-4689ae6d305348698e6399c1f080b63b
Source dataset
uspto-grants-2011_08
Patent number
US07994351B2

Reaction notes

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