HCID 68539826, compound → HCID 68536371, compound

HRID 1992860Notes

Reaction equation

HRID 1992860 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH:5]=[C:6]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)[CH:7]([CH3:9])[CH3:8])[CH3:2].[H][H]>C(O)C.[Pd]>[CH3:9][CH:7]([CH3:8])[CH:6]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:19]

Participants

5

Reactant 2

HCID 68539826HCID 68539826, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68536371HCID 68536371, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The oily mixture containing (65) was dissolved in ethanol (50 mL) and 10% Pd/C (200 mg) was added. The mixture was hydrogenated at room temperature using a hydrogen balloon overnight. Filtered through celite, the filtrate was concentrated to give 1.72 g of compound (66) (41% from the ketone) of the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 0.89 (d, J=7.4 Hz, 3H), 0.91 (d, J=7.6 Hz, 3H), 1.21 (t, J=7.2 Hz, 3H), 1.70-1.80 (m, 1H), 2.10-2.20 (m, 2H), 2.20-2.30 (m, 1H), 2.44 (dd, J1=13.6 Hz, J2=7.4 Hz, 1H), 2.64 (dd, J1=13.7 Hz, J2=6.2 Hz, 1H), 3.79 (s, 3H), 4.04 (q, J=7.2 Hz, 2H), 6.70-6.80 (m, 3H), 7.15-7.20 (m, 1H).

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationFiltered through celite
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c176f89998d04db28d3772687b2a3ec1
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

Loading…