HCID 58238565, compound → HCID 58238605, compound

HRID 45441Notes

Reaction equation

HRID 45441 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]([C:21]1[CH:22]=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[CH:24]=[CH:25][CH:26]=1)=[CH2:20])C1C=CC=CC=1>CO.C(OCC)(=O)C.[Pd]>[C:15]([C:14]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:19]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)[CH:22]=2)[CH3:20])[C:9]=1[OH:8])([CH3:16])([CH3:17])[CH3:18]

Participants

5

Reactant 1

HCID 58238565HCID 58238565, compound

Product 1

HCID 58238605HCID 58238605, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5 (1.12 g, 2.67 mmol) in methanol (40 mL) and ethyl acetate (80 mL) was treated with 20% palladium on activated carbon (0.2 g, 0% wet) and hydrogenated in a Parr shaker at 10 psi for 3.5 hr. The catalyst was filtered off and washed with ethyl acetate. The solvent was removed on a rotary evaporator and the crude product was purified by chromatography on silica (80 g) with 2% ethyl acetate in hexane (1 L), then 4% (2 L) to yield pure A2 (0.75 g, 85%).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with ethyl acetate
  3. customThe solvent was removed on a rotary evaporator
  4. customthe crude product was purified by chromatography on silica (80 g) with 2% ethyl acetate in hexane (1 L)

Sources & evidence

ORD record
ord-3ec31c8f950b4e26a67bb295e22f3047
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

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