HCID 57443794, compound → HCID 57443795, compound

HRID 1676900Notes

Reaction equation

HRID 1676900 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:19][CH2:18][C:17](=[O:20])[CH2:16]2)=[CH:11][CH:10]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]>C(O)=O.[Pd].CO>[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:19][CH2:18][C:17](=[O:20])[CH2:16]2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 1

HCID 57443794HCID 57443794, compound

Product 1

HCID 57443795HCID 57443795, compound

Reagents, catalysts & solvents 3

HCID 284Formic AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Several drops of formic acid and catalytic amount 5% Pd/C was added to a 25 mL flask charged with 10 mL methanol and 1.34 g (5 mmol) of 2. The reaction vessel was flushed with H2, 3 times, and then mounted with a H2 balloon. After two days of hydrogenolysis, the solute was filtered through a pad of silica, and concentrated to provide a yellow oil. 1.32 g (98%) product was collected. 1H NMR (CDCl3) δ 7.18 (s, 4H, ArH), 3.38 (m, 1H, ArCHCC), 2.60 (t, 2H, CCCH2CH2), 2.45-1.91 (m, 6H, cyclo-pentyl), 1.64-1.15 (m, 12H, CH2), 0.90 (t, 3H, CH3); 13C NMR (CDCl3) δ 220, 142, 140, 129, 127, 46, 42, 39, 36, 32, 32, 32, 30, 30, 29, 23, 14.

Workup

  1. customThe reaction vessel was flushed with H2, 3 times
  2. filtrationthe solute was filtered through a pad of silica
  3. concentrationconcentrated
  4. customto provide a yellow oil
  5. custom1.32 g (98%) product was collected

Sources & evidence

ORD record
ord-46d275231bc74b19ae4e43e03866c95b
Source dataset
uspto-grants-2011_08
Patent number
US08008286B2

Reaction notes

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