HCID 58238626, compound → HCID 136177198, compound

HRID 1037658Notes

Reaction equation

HRID 1037658 reaction equation
C([O:8][C:9]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH2:26])[N:20]=1)C1C=CC=CC=1>C(O)C.[Pd]>[C:15]([C:14]1[CH:13]=[CH:12][CH:11]=[C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:26])[N:20]=2)[C:9]=1[OH:8])([CH3:16])([CH3:17])[CH3:18]

Participants

4

Reactant 1

HCID 58238626HCID 58238626, compound

Product 1

HCID 136177198HCID 136177198, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Compound 13 (1.0 g, 2.38 mmol, 1.0 equiv) was dissolved in ethanol (30 mL) and 10% palladium (50% aqueous) on carbon (0.2 g) was added. The material was shaken on a Parr hydrogenator under a hydrogen atmosphere (30 psi) for 3 hr. The reaction was filtered through a bed of Celite and rinsed with dichloromethane (100 mL). The product was absorbed onto silica gel (5 g) by concentration under reduced pressure. This material was purified on a silica gel column (50 g) by eluting with ethyl acetate (0.5%) in heptanes (800 mL). The desired product was isolated pure in 36% yield (0.3 g).

Workup

  1. filtrationThe reaction was filtered through a bed of Celite
  2. washrinsed with dichloromethane (100 mL)
  3. customThe product was absorbed onto silica gel (5 g) by concentration under reduced pressure
  4. customThis material was purified on a silica gel column (50 g)
  5. washby eluting with ethyl acetate (0.5%) in heptanes (800 mL)

Sources & evidence

ORD record
ord-cbc63a1e8d2c424d9ae8187565055175
Source dataset
uspto-grants-2013_10
Patent number
US08546501B2

Reaction notes

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