HCID 86609594, compound → HCID 66858583, compound

HRID 1661125Notes

Reaction equation

HRID 1661125 reaction equation
[CH3:1][O:2][C:3](=[O:36])[CH:4]=[CH:5][CH2:6][C@H:7]1[C@H:12]2[C@H:13]3[C@H:22]([CH2:23][CH2:24][C@:10]2([CH3:11])[C:9](=[O:35])[CH2:8]1)[C:21]1[CH:20]=[C:19]([O:25][CH3:26])[C:18]([O:27]CC2C=CC=CC=2)=[CH:17][C:16]=1[CH2:15][CH2:14]3>C1COCC1.CO.[Pd]>[CH3:1][O:2][C:3](=[O:36])[CH2:4][CH2:5][CH2:6][C@H:7]1[C@H:12]2[C@H:13]3[C@H:22]([CH2:23][CH2:24][C@:10]2([CH3:11])[C:9](=[O:35])[CH2:8]1)[C:21]1[CH:20]=[C:19]([O:25][CH3:26])[C:18]([OH:27])=[CH:17][C:16]=1[CH2:15][CH2:14]3

Participants

5

Reactant 1

HCID 86609594HCID 86609594, compound

Product 1

HCID 66858583HCID 66858583, compoundYield 1,460%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(3-Benzyloxy-2-methoxy-17-oxo-estra-1,3,5(10)-trien-15β-yl)-but-2-enoic acid methyl ester (17.3 g, 2.36 mmol) in THF (440 ml) and MeOH (440 ml) was purged with H2 (balloon). Then Pd (10% on carbon, 50% H2O) (1.80 g) was added, and the mixture obtained was stirred under H2 pressure for over night. The reaction mixture was filtered over two filter papers and concentrated in vacuo to yield the desired compound (VIIβ-(C2-B)-3a-1) (13.8 g, 97%), which represents a compound falling under the scope of the present invention.

Workup

  1. customthe mixture obtained
  2. filtrationThe reaction mixture was filtered over two
  3. filtrationfilter papers
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-16eefec7986b4349bea522f6bacce148
Source dataset
uspto-grants-2011_10
Patent number
US08030298B2

Reaction notes

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