HCID 57701073, compound → HCID 25267395, compound

HRID 422883Notes

Reaction equation

HRID 422883 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]23[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]=[C:19]2[O:18][C:17]2[CH:25]=[CH:26][CH:27]=[C:28]([F:29])[C:16]3=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].C(OCC)(=O)C.C(O)C>[F:29][C:28]1[C:16]2[C:15]3([C:12]4[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=4)[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]=[C:19]3[O:18][C:17]=2[CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 1

HCID 57701073HCID 57701073, compound

Product 1

HCID 25267395HCID 25267395, compoundYield 69.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

10% Palladium on activated carbon (few mg) was added to a solution of 22 (15 mg) in ethyl acetate (2 mL) and ethanol (2 mL). A balloon filled with H2 was fitted and H2 was bubbled through the solution for 15 s. The mixture was filtered after 15 min, TLC indicated 50% conversion of 22. Work-up by flash chromatography (eluent: dichloromethane −>5% ethyl acetate in dichloromethane) afforded 8 mg of the title product. Starting material (5 mg) was recovered. LC-MS confirmed m/z=295 (M−1). 1H-NMR (400 MHz, CDCl3): δ ppm 7.49-7.46 (m, 2H), 7.05-7.00 (m, 1H), 6.81-6.79 (m, 2H), 6.61-6.59 (m, 1H), 6.53-6.48 (m, 1H), 5.73 (dd, J=4.8, 9.2 Hz, 1H), 3.07-3.02 (m, 1H), 2.00-1.20 (m, 8H).

Workup

  1. additionA balloon filled with H2
  2. customwas fitted
  3. customH2 was bubbled through the solution for 15 s
  4. filtrationThe mixture was filtered after 15 min

Sources & evidence

ORD record
ord-b63a32226da048f79d30aef1de54ce4a
Source dataset
uspto-grants-2012_01
Patent number
US08101651B2

Reaction notes

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