Pyridine → 3-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidine-1-carboxylic Acid Benzyl Ester

HRID 1893046

Reaktionsgleichung

Reaktionsgleichung von HRID 1893046
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([CH2:16][OH:17])[CH:13]([OH:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24]N=1)C.[C:28](Cl)(C1C=CC=CC=1)([C:37]1[CH:44]=[CH:43][C:40]([O:41][CH3:42])=[CH:39][CH:38]=1)[C:29]1[CH:36]=[CH:35][C:32]([O:33][CH3:34])=[CH:31][CH:30]=1.N1C=CC=C[CH:53]=1>>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH:13]([OH:18])[CH:14]([CH:16]([C:24]2[CH:53]=[CH:22][CH:27]=[CH:26][CH:25]=2)[O:17][CH:28]([C:29]2[CH:36]=[CH:35][C:32]([O:33][CH3:34])=[CH:31][CH:30]=2)[C:37]2[CH:38]=[CH:39][C:40]([O:41][CH3:42])=[CH:43][CH:44]=2)[CH2:15]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 4

HCID 1049Pyridine2×HCID 218852-DimethylaminopyridineHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 230620493-Hydroxy-4-hydroxymethyl-pyrrolidine-1-carboxylic Acid Benzyl Ester

Produkt 1

HCID 1317282233-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidine-1-carboxylic Acid Benzyl Ester

Versuchsvorschrift

Referring to scheme 18, compound 74 (4.39 g, 17.5 mmol) was co-evaporated with anhydrous pyridine three times and then dissolved in pyridine (30 mL) To this solution dimethylamino pyridine (0.213 g, 1.75 mmol) and DMT-Cl (6.22 g, 18.4 mmol, 1.05 equiv.) were added at room temperature. The reaction mixture was stirred at room temperature for 16 h. The excess DMT-Cl was quenched by the addition of methanol (10 mL) The solution was dried under reduced pressure. To the residue was suspended in ethyl acetate (300 mL) and washed with saturated bicarbonate solution, brine and water. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated. The crude product was obtained after removal of the solvent. Upon purification over silica gel using 3% MeOH/DCM compound 75 (8.46 g, 87%) was obtained as white foamy solid.

Aufarbeitung

  1. additionwere added at room temperature
  2. customThe excess DMT-Cl was quenched by the addition of methanol (10 mL) The solution
  3. customwas dried under reduced pressure
  4. washwashed with saturated bicarbonate solution, brine and water
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-930a7747d9d84226a7c30137659e52e6
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507661B2

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