HCID 69108764, compound → HCID 69113200, compound

HRID 749014Notes

Reaction equation

HRID 749014 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH:19]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:20]([OH:22])=[O:21])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[H][H]>[Ni].CO>[C:27]([O:26][C:24]([NH:23][CH:19]([CH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]2[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:31])=[CH:7][CH:8]=2)=[CH:13][CH:14]=1)[C:20]([OH:22])=[O:21])=[O:25])([CH3:29])([CH3:30])[CH3:28]

Participants

5

Reactant 2

HCID 69108764HCID 69108764, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69113200HCID 69113200, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Raney nickel 2800 (4.0 g) was added to a degassed solution of the unsaturated ester 43 (4.1 g) in MeOH (150 mL) and the resulting suspension was treated with hydrogen at atmospheric pressure for 18 h. The suspension was filtered over a Celite® bed and concentrated. Flash chromatography (30-50% ethyl acetate in hexane containing 1% acetic acid) of the resulting residue gave the desired saturated ester 44 (3.8 g, 94.5%). 1H NMR (400 MHz, DMSO-d6): 7.54 (d, J=7.6 Hz, 4H), 7.31 (overlapped d, J=8.8 Hz, 2H), 7.29 (overlapped d, J=8.4 Hz, 2H), 4.12 (m, 1H), 3.58 (s, 3H), 2.87 (t, J=7.6 Hz, 2H), 2.65 (t, J 7.6 Hz, 2H), 1.31 (s, 9H).

Workup

  1. filtrationThe suspension was filtered over a Celite® bed
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-577ca1f72a444a3985afb535bbdd5c32
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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