HCID 69108109, compound → HCID 69230869, compound

HRID 749029Notes

Reaction equation

HRID 749029 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:21]([OH:23])=[O:22])=[CH:15][CH:14]=1.[H][H]>[Ni].CO>[C:28]([O:27][C:25]([NH:24][CH:20]([CH2:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:32])=[CH:14][CH:15]=1)[C:21]([OH:23])=[O:22])=[O:26])([CH3:30])([CH3:31])[CH3:29]

Participants

5

Reactant 2

HCID 69108109HCID 69108109, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69230869HCID 69230869, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Raney nickel 2800 (2.5 g) was added to a degassed solution of the unsaturated ester 59 (2.5 g) in MeOH (50.0 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 60 (2.2 g, 98%). 1H NMR (400 MHz, DMSO-d6): 12.63 (s, 1H), 7.31 (dd, J=7.6 and 1.6 Hz, 1H), 7.21 (m, 3H), 7.08 (m, 2H), 6.85 (d, J=8.4 Hz, 2H), 6.77 (d, J=7.6 Hz, 1H), 4.06 (m, 1H), 3.55 (s, 3H), 3.0 (m, 1H), 2.84 (t, J=7.2 Hz, 2H) 2.76 (m, 1H) 2.61 (t, J=7.2 Hz, 2H), 1.31 (s, 9H)

Workup

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

Sources & evidence

ORD record
ord-b2a1842f3d8c4b198be49d42f935bf1c
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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