HCID 70010354, compound → HCID 11832397, compound

HRID 433048Notes

Reaction equation

HRID 433048 reaction equation
C([O:8][C:9]1[CH:25]=[CH:24][C:12]([C:13]([O:15][C@H:16]([CH3:23])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:14])=[C:11]([F:26])[CH:10]=1)C1C=CC=CC=1>[Pd].C(OCC)(=O)C>[OH:8][C:9]1[CH:25]=[CH:24][C:12]([C:13]([O:15][C@H:16]([CH3:23])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:14])=[C:11]([F:26])[CH:10]=1

Participants

4

Reactant 1

HCID 70010354HCID 70010354, compound

Product 1

HCID 11832397HCID 11832397, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

10% Palladium on charcoal (0.3 g), was added to a solution of compound 23 (8.20 g, 23 mmol) in ethyl acetate (200 ml). The solution was evacuated and left stirring with hydrogen at atmospheric pressure for 24 h. The catalyst was filtered off and the solvent removed in vacuo to yield a yellow oil which was purified by column chromatography (dichloromethane) on silica to yield the pure colourless oil. Yield 4.68 g (76%). [α]D=−28.39° at 25° C.

Workup

  1. customThe solution was evacuated
  2. waitleft
  3. filtrationThe catalyst was filtered off
  4. customthe solvent removed in vacuo
  5. customto yield a yellow oil which
  6. customwas purified by column chromatography (dichloromethane) on silica
  7. customto yield the pure colourless oil
  8. customat 25° C.

Sources & evidence

ORD record
ord-3f0fe165a8f74dd89dbc66c438bf4830
Source dataset
uspto-grants-2003_12
Patent number
US06666989B1

Reaction notes

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