Ethyl [(phenoxycarbonyl)oxy]acetate → 2-(Ethyloxy)-2-oxoethyl 4-[(1-naphthalenyloxy)methyl]-1-piperidinecarboxylate

HRID 912738

Reaktionsgleichung

Reaktionsgleichung von HRID 912738
[C:1]1([O:11][CH2:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C1([O:25][C:26]([O:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=O)C=CC=CC=1>C1(C)C=CC=CC=1>[C:1]1([O:11][CH2:12][CH:13]2[CH2:14][CH2:15][N:16]([C:26]([O:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:25])[CH2:17][CH2:18]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 12094709Ethyl [(phenoxycarbonyl)oxy]acetateHCID 247000964-[(1-Naphthyloxy)methyl]piperidine

Produkt 1

HCID 674160052-(Ethyloxy)-2-oxoethyl 4-[(1-naphthalenyloxy)methyl]-1-piperidinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 2.75 g (11.4 mmol) of 4-[(1-naphthalenyloxy)methyl]piperidine, prepared in Step 7.2., and 2.56 g (11.4 mmol) of ethyl [(phenyloxy-carbonyl)oxy]acetate, prepared in accordance with Example 1.1, in 80 ml of toluene is heated at 50° C. overnight. It is evaporated to dryness and the residue is taken up in a mixture of water, dichloromethane and saturated aqueous sodium hydrogen carbonate solution. The organic phase is decanted, dried over sodium sulfate and evaporated to dryness. The product is purified by chromatography on silica gel, eluting with a 50/50 mixture of cyclohexane and dichloromethane and then with dichloromethane and with a 95/5 mixture of dichloromethane and ethyl acetate. This gives 2.05 g of product in oil form, which is used as it is in the following step.

Aufarbeitung

  1. customIt is evaporated to dryness
  2. additionthe residue is taken up in a mixture of water, dichloromethane and saturated aqueous sodium hydrogen carbonate solution
  3. customThe organic phase is decanted
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customThe product is purified by chromatography on silica gel
  7. washeluting with a 50/50 mixture of cyclohexane and dichloromethane
  8. additionwith dichloromethane and with a 95/5 mixture of dichloromethane and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-2c69b4bff0ca4bb0be7ba54da775201e
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026258B2

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