Ammonia → 2-Amino-2-oxoethyl 4-[(1-naphthalenyl-oxy)methyl]-1-piperidinecarboxylate

HRID 2116603

Reaktionsgleichung

Reaktionsgleichung von HRID 2116603
[C:1]1([O:11][CH2:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]([O:25]CC)=O)=[O:20])[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.[NH3:28]>CO>[C:1]1([O:11][CH2:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]([NH2:28])=[O:25])=[O:20])[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

Komponenten

4

Edukt 2

HCID 222AmmoniaHCID 674160052-(Ethyloxy)-2-oxoethyl 4-[(1-naphthalenyloxy)methyl]-1-piperidinecarboxylate

Produkt 1

HCID 113138682-Amino-2-oxoethyl 4-[(1-naphthalenyl-oxy)methyl]-1-piperidinecarboxylateAusbeute 83,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

1.0 g (2.69 mmol) of 2-(ethyloxy)-2-oxoethyl 4-[(1-naphthalenyloxy)methyl]-1-piperidinecarboxylate, prepared in Step 7.3., is dissolved in 12 ml of a 7N solution of ammonia (84 mmol) in methanol. The solution is left to react at ambient temperature for 3 days. It is evaporated to dryness and the residue is purified by chromatography on silica gel, eluting with a 90/10 then 80/20, 70/30 and 50/50 mixture of dichloromethane and ethyl acetate and then with a 95/5 mixture of ethyl acetate and methanol. The eluate is subsequently recrystallized from ethyl acetate, to give 0.77 g of product.

Aufarbeitung

  1. waitThe solution is left
  2. customto react at ambient temperature for 3 days
  3. customIt is evaporated to dryness
  4. customthe residue is purified by chromatography on silica gel
  5. washeluting with a 90/10
  6. addition80/20, 70/30 and 50/50 mixture of dichloromethane and ethyl acetate
  7. additionwith a 95/5 mixture of ethyl acetate and methanol
  8. customThe eluate is subsequently recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-14fbc7b7c40d47c7827198996ecc688e
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07439257B2

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