Propargyl bromide → Methyl 2-propargyloxy-4-(N-t-butyloxycarbonyl-4-piperidinyloxy)benzoate

HRID 1377723Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1377723
[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:26](Br)[C:27]#[CH:28].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:28]([O:1][C:2]1[CH:11]=[C:10]([O:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])[C:27]#[CH:26]

Komponenten

5

Edukt 3

HCID 7842Propargyl bromideHCID 10796Cesium carbonateHCID 105940774-(N-t-Butoxycarbonyl-4-piperidinyloxy)-2-hydroxybenzoic acid methyl ester

Produkt 1

HCID 22914696Methyl 2-propargyloxy-4-(N-t-butyloxycarbonyl-4-piperidinyloxy)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Methyl 2-hydroxy-4-(N-t-butyloxycarbonyl-4-piperidinyloxy)benzoate (0.5 gm, 1.42 mmol) from Step 1 of Example 25 was dissolved in DMF (5 mL) and propargyl bromide (186 mg, 1.56 mmol) was added followed by cesium carbonate (925 mg, 2 eq.) and the mixture was stirred 16 hrs. The solids were removed by filtration and the filtrate solvents were removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 1:1 ethyl acetate:hexanes as eluant. Methyl 2-propargyloxy-4-(N-t-butyloxycarbonyl-4-piperidinyloxy)benzoate was obtained as a gum.

Aufarbeitung

  1. customThe solids were removed by filtration
  2. customthe filtrate solvents were removed under reduced pressure
  3. customThe residue was purified by pressurized silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a37e663377f94bb0a598daf7cfaf81c3
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05665719

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