HCID 13887610, compound → HCID 57326244, compound

HRID 388726Notes

Reaction equation

HRID 388726 reaction equation
[CH3:1][C@@:2]12[C@@H:10]([C@H:11]([CH3:19])/[CH:12]=[CH:13]/[C@H:14]([CH3:18])[CH:15]([CH3:17])[CH3:16])[CH2:9][CH2:8][C@H:7]1[C@@H:6]([OH:20])[CH2:5][CH2:4][CH2:3]2>C(O)(=O)C.[Pt]>[CH3:1][C@@:2]12[C@@H:10]([C@H:11]([CH3:19])[CH2:12][CH2:13][C@H:14]([CH3:18])[CH:15]([CH3:16])[CH3:17])[CH2:9][CH2:8][C@H:7]1[C@@H:6]([OH:20])[CH2:5][CH2:4][CH2:3]2

Participants

4

Reactant 1

HCID 13887610HCID 13887610, compound

Product 1

HCID 57326244HCID 57326244, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolvent

Procedure

The compound of Example 7A (400 mg, 1.4 mmol) was dissolved in 20 mL of acetic acid and hydrogenated using a 10% platinum on carbon catalyst. After purging with nitrogen and filtering to remove catalyst, the solvent was removed in vacuo, and the residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was washed with brine and dried over sodium sulfate. The solvents were removed in vacuo, and the residue was purified by chromatography on an Analogix Intelliflash 280™, eluting with a gradient from 5% to 30% ethyl acetate in hexanes to furnish the titled compound, 390 mg.

Workup

  1. customAfter purging with nitrogen
  2. filtrationfiltering
  3. customto remove catalyst
  4. customthe solvent was removed in vacuo
  5. customthe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  6. washThe organic phase was washed with brine
  7. dry with materialdried over sodium sulfate
  8. customThe solvents were removed in vacuo
  9. customthe residue was purified by chromatography on an Analogix Intelliflash 280™
  10. washeluting with a gradient from 5% to 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-27c2fcfa1a1946079b5e00f7d4ef85eb
Source dataset
uspto-grants-2013_02
Patent number
US08377913B2

Reaction notes

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