HCID 86609594, compound → HCID 66858583, compound

HRID 2088522Notes

Reaction equation

HRID 2088522 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-13d437d2d4a149469632c2afb863e482
Source dataset
uspto-grants-2013_05
Patent number
US08435973B2

Reaction notes

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