(E)-Methyl 3alpha-acetoxy-5beta-chol-9(11),16,22-trien-24-oate → (R)-Methyl 4-((3R,5R,8S,10S,13R,14S,17R)-3-acetoxy-10,13-dimethyl-2,3,4,5,6,7,8,10,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate

HRID 1671721Notes

Reaction equation

HRID 1671721 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][CH2:24][C@@:23]2([CH3:31])[C@H:11]3[CH2:12][CH:13]=[C:14]2[C@H:15]([CH3:22])/[CH:16]=[CH: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:26]2=[CH:25][CH2:24][C@@:23]2([CH3:31])[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 25145011(E)-Methyl 3alpha-acetoxy-5beta-chol-9(11),16,22-trien-24-oate

Product 1

HCID 59365567(R)-Methyl 4-((3R,5R,8S,10S,13R,14S,17R)-3-acetoxy-10,13-dimethyl-2,3,4,5,6,7,8,10,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoateYield 86.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of compound 1.7a (3 g, 7 mmol) in EtOAc (60 mL) was added 10% Pd/C (300 mg, 10% wt/wt), and the resulting slurry was hydrogenated in a Pan apparatus (70 psi) for 14-16 h. At this point the reaction was determined to be complete by TLC (10% ethyl acetate in hexanes). The mixture was filtered through a small plug of Celite® and the solvent was removed under vacuum, affording compound 1.8a (2.6 g, 86%) 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-4757fb97a69a4e7ea6712faa9f8f70da
Source dataset
uspto-grants-2011_08
Patent number
US07994351B2

Reaction notes

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