Ethanol → (E)-1-[(1R,2S)-2-hydroxyindan-1-yl]-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]piperidin-2-one

HRID 1446502Notes

Reaction equation

HRID 1446502 reaction equation
C(O)C.C([O:6][C:7](=O)/[C:8](=[CH:23]/[C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]2)=[C:26]([O:36][CH3:37])[CH:25]=1)/[CH2:9][CH2:10][CH2:11][NH:12][C@@H:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][C@@H:14]1[OH:22])C.[OH-].[Na+].O>C(OCC)(=O)C>[OH:22][C@H:14]1[CH2:15][C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@H:13]1[N:12]1[CH2:11][CH2:10][CH2:9]/[C:8](=[CH:23]\[C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]3)=[C:26]([O:36][CH3:37])[CH:25]=2)/[C:7]1=[O:6]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 66961755(E)-5-[(1R,2S)-2-hydroxyindan-1-ylamino]-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]valeric acid ethyl ester

Product 1

HCID 59170845(E)-1-[(1R,2S)-2-hydroxyindan-1-yl]-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]piperidin-2-oneYield 72.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To an ethanol (2.0 mL) solution of (E)-5-[(1R,2S)-2-hydroxyindan-1-ylamino]-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]valeric acid ethyl ester (120 mg), 2N sodium hydroxide solution (1.0 mL) was added. After carrying out heat-refluxing of the reaction solution for 30 minutes and confirming disappearance of the starting materials, water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (Carrier: Chromatorex™ NH, elution solvent:heptane-ethyl acetate=1:1→ethyl acetate→ethyl acetate:ethanol=10:1), and 78.9 mg of the title compound was obtained. The physical properties of the compound are as follows.

Workup

  1. temperatureAfter carrying out heat-refluxing of the reaction solution for 30 minutes
  2. additionwere added to the reaction solution
  3. customthe organic layer was partitioned
  4. washAfter the obtained organic layer was washed with a saturated saline solution, it
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (Carrier: Chromatorex™ NH, elution solvent:heptane-ethyl acetate=1:1→ethyl acetate→ethyl acetate:ethanol=10:1)

Sources & evidence

ORD record
ord-bf7666589e484c6590fbe7525161155c
Source dataset
uspto-grants-2010_02
Patent number
US07667041B2

Reaction notes

Loading…