HCID 86609595, compound → HCID 66859868, compound

HRID 1661127Notes

Reaction equation

HRID 1661127 reaction equation
[CH3:1][O:2][C:3](=[O:37])[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:36])[CH2:8]1)[C:21]1[CH:20]=[C:19]([O:25][CH2:26][CH3:27])[C:18]([O:28]CC2C=CC=CC=2)=[CH:17][C:16]=1[CH2:15][CH2:14]3>C1COCC1.CO.[Pd]>[CH3:1][O:2][C:3](=[O:37])[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:36])[CH2:8]1)[C:21]1[CH:20]=[C:19]([O:25][CH2:26][CH3:27])[C:18]([OH:28])=[CH:17][C:16]=1[CH2:15][CH2:14]3

Participants

5

Reactant 1

HCID 86609595HCID 86609595, compound

Product 1

HCID 66859868HCID 66859868, compoundYield 106.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(3-Benzyloxy-2-ethoxy-17-oxo-estra-1,3,5(10)-trien-15α-yl)but-2-enoic acid methyl ester (3.17 g, 6.30 mmol) was dissolved in THF (80 ml) and MeOH (80 ml). Pd/C 10% (50% in water, 0.3 g) was added. The mixture was stirred at 1 atm H2 (balloon) at RT for 48 h. The mixture was filtered over Celite. The filter cake was rinsed with MeOH (200 ml) and the filtrate was concentrated in vacuo to provide 2.8 g (6.72 mmol, >100%) of a greenish solid.

Workup

  1. filtrationThe mixture was filtered over Celite
  2. washThe filter cake was rinsed with MeOH (200 ml)
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ab0b6cd986d84e859749cd5bcc48e1b8
Source dataset
uspto-grants-2011_10
Patent number
US08030298B2

Reaction notes

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